Substituted oxadiazoles for combating phytopathogenic fungi

ABSTRACT

The present invention relates to novel trifluoromethyloxadiazoles of the formula I, or the N-oxides, or the agriculturally useful salts thereof; and to their use for controlling phytopathogenic fungi; and to a method for combating phytopathogenic harmful fungi, which process comprises treating the fungi, the plants, the soil or seeds to be protected against fungal attack, with an effective amount of at least one compound of the formula I, or an N-oxide, or an agriculturally acceptable salt thereof; and to agrochemical compositions comprising at least one compound of the formula I; and to agrochemical compositions further comprising seeds.

This application is a National Stage application of InternationalApplication No. PCT/EP2018/053553, filed Feb. 13, 2018. This applicationalso claims priority under 35 U.S.C. § 119 to European PatentApplication No. 17157051.8, filed Feb. 21, 2017.

The present invention relates to novel trifluoromethyloxadiazoles of theformula I, or the N-oxides, or the agriculturally useful salts thereof;and to their use for controlling phytopathogenic fungi; and to a methodfor combating phytopathogenic harmful fungi, which process comprisestreating the fungi, the plants, the soil or seeds to be protectedagainst fungal attack, with an effective amount of at least one compoundof the formula I, or an N-oxide, or an agriculturally acceptable saltthereof; and to agrochemical compositions comprising at least onecompound of the formula I; and to agrochemical compositions furthercomprising seeds.

EP 276432 A2 relates to 3-phenyl-5-trifluoromethyloxadiazole derivativesand to their use to combat phytopathogenic microorganisms. WO2015/185485 A1 describes similar derivatives oftrifluoromethyloxadiazoles and their use to combat phytopathogenicmicroorganisms.

WO 97/30047 A1 describes certain trifluoromethyloxadiazole analogueswith fungicidal activity.

WO 2017/213252 A1 discloses further oxadiazole compounds and their useas pesticides.

In many cases, in particular at low application rates, the fungicidalactivity of known fungicidal compounds is unsatisfactory. Based on this,it was an objective of the present invention to provide compounds havingimproved activity and/or a broader activity spectrum againstphytopathogenic fungi. This objective is achieved by the oxadiazoles ofthe formula I and/or their agriculturally useful salts for controllingphytopathogenic fungi.

The compounds described herein differ from compounds known in the priorart in the constitution of the group —CR³R⁴—NR²-L-R¹.

Accordingly, the present invention relates to compounds of the formulaI, or the N-oxides, or the agriculturally acceptable salts thereof

wherein:

-   R^(A) is independently selected from the group consisting of    halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and    C₁-C₆-haloalkoxy;-   n is 0, 1 or 2;-   L is —(C═S)— or —S(═O)_(p)—;-   p is 0, 1 or 2;-   R¹ is C₁-C₆-alkyl or C₁-C₆-alkoxy; wherein any of the aliphatic    groups are unsubstituted or substituted with 1, 2, 3, 4, 5 or up to    the maximum possible number of identical or different radicals    selected from the group consisting of hydroxy, cyano, C₁-C₆-alkyl,    C₁-C₆-alkoxy and C₃-C₈-cycloalkyl;-   R² is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    C₁-C₆-alkoxy, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkenyl,    C₃-C₈-cycloalkyl-C₁-C₄-alkyl, phenyl-C₁-C₄-alkyl, phenyl,    C(═O)—(C₁-C₆-alkyl) or C(═O)—(C₁-C₆-alkoxy); and wherein any of the    aliphatic or cyclic groups are unsubstituted or substituted with 1,    2, 3 or up to the maximum possible number of identical or different    radicals selected from the group consisting of halogen, hydroxy,    cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy and C₃-C₈-cycloalkyl;-   R³, R⁴ independently of each other are selected from the group    consisting of hydrogen, halogen, cyano, C₁-C₄-alkyl, C₁-C₄-alkenyl,    C₁-C₄-alkynyl, C₁-C₄-haloalkyl and C₁-C₄-alkoxy;-   or R³ and R⁴ together with the carbon atom to which they are bound    form a saturated 3- to 7-membered carbocycle or a saturated 3- to    6-membered heterocycle; wherein the saturated heterocycle includes    beside carbon atoms 1, 2 or 3 heteroatoms independently selected    from the group consisting of N, O and S as ring member atoms; and    wherein said N ring member atom is substituted with the group R^(N);    wherein    -   R^(N) is hydrogen, C₁-C₆-alkyl or halogen;    -   and wherein said S ring member atom is unsubstituted or        substituted with 1 or 2 oxo radicals; and wherein one or two CH₂        groups of the saturated carbocycle or of the saturated        heterocycle may be replaced by one or two groups independently        selected from —C(═O)— and —C(═S)—; and wherein the carbon ring        member atoms of the saturated carbocycle or of the saturated        heterocycle are unsubstituted or substituted with a total number        of 1, 2, 3, 4 or up to the maximum possible number of identical        or different radicals selected from the group consisting of        halogen, cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy and C₃-C₈-cycloalkyl;

with the exception of compounds of the formula I wherein R³ and R⁴ bothare hydrogen.

Agriculturally acceptable salts of the compounds of the formula Iencompass especially the salts of those cations or the acid additionsalts of those acids whose cations and anions, respectively, have noadverse effect on the fungicidal action of the compounds 1. Suitablecations are thus in particular the ions of the alkali metals, preferablysodium and potassium, of the alkaline earth metals, preferably calcium,magnesium and barium, of the transition metals, preferably manganese,copper, zinc and iron, and also the ammonium ion which, if desired, maybe substituted with one to four C₁-C₄-alkyl substituents and/or onephenyl or benzyl substituent, preferably diisopropylammonium,tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium,furthermore phosphonium ions, sulfonium ions, preferablytri(C₁-C₄-alkyl)sulfonium, and sulfoxonium ions, preferablytri(C₁-C₄-alkyl)sulfoxonium.

Anions of acceptable acid addition salts are primarily chloride,bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate,hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate,hexafluorosilicate, hexafluorophosphate, benzoate, and the anions ofC₁-C₄-alkanoic acids, preferably formate, acetate, propionate andbutyrate. They can be formed by reacting a compound I with an acid ofthe corresponding anion, preferably of hydrochloric acid, hydrobromicacid, sulfuric acid, phosphoric acid or nitric acid.

Compounds of the formula I can exist as one or more stereoisomers. Thevarious stereoisomers include enantiomers, diastereomers, atropisomersarising from restricted rotation about a single bond of asymmetricgroups and geometric isomers. They also form part of the subject matterof the present invention. One skilled in the art will appreciate thatone stereoisomer may be more active and/or may exhibit beneficialeffects when enriched relative to the other stereoisomer(s) or whenseparated from the other stereoisomer(s). Additionally, the skilledartisan knows how to separate, enrich, and/or to selectively preparesaid stereoisomers. The compounds of the invention may be present as amixture of stereoisomers, e.g. a racemate, individual stereoisomers, oras an optically active form.

Compounds of the formula I can be present in different crystalmodifications whose biological activity may differ. They also form partof the subject matter of the present invention.

In respect of the variables, the embodiments of the intermediatesobtained during preparation of compounds I correspond to the embodimentsof the compounds of formula I. The term “compounds I” refers tocompounds of formula I.

In the definitions of the variables given above, collective terms areused which are generally representative for the substituents inquestion. The term “C_(n)-C_(m)” indicates the number of carbon atomspossible in each case in the substituent or substituent moiety inquestion.

The term “halogen” refers to fluorine, chlorine, bromine and iodine.

The term “C₁-C₆-alkyl” refers to a straight-chained or branchedsaturated hydrocarbon group having 1 to 6 carbon atoms, for examplemethyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl,2-methylpropyl, and 1,1-dimethylethyl.

The term “C₂-C₆-alkenyl” refers to a straight-chain or branchedunsaturated hydrocarbon radical having 2 to 6 carbon atoms and a doublebond in any position, such as ethenyl, 1-propenyl, 2-propenyl (allyl),1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl,2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl.

The term “C₂-C₆-alkynyl” refers to a straight-chain or branchedunsaturated hydrocarbon radical having 2 to 6 carbon atoms andcontaining at least one triple bond, such as ethynyl, 1-propynyl,2-propynyl (propargyl), 1-butynyl, 2-butynyl, 3-butynyl,1-methyl-2-propynyl.

The term “C₁-C₆-haloalkyl” refers to a straight-chained or branchedalkyl group having 1 to 6 carbon atoms (as defined above), wherein someor all of the hydrogen atoms in these groups may be replaced by halogenatoms as mentioned above, for example chloromethyl, bromomethyl,dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl,2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl,2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl,3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, CH₂—C₂F₅,CF₂—C₂F₅, CF(CF₃)₂, 1-(fluoromethyl)-2-fluoroethyl,1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl,4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl.

The term “C₁-C₆-alkoxy” refers to a straight-chain or branched alkylgroup having 1 to 6 carbon atoms (as defined above) which is bonded viaan oxygen, at any position in the alkyl group, for example methoxy,ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy,2-methylpropoxy or 1,1-dimethylethoxy.

The term “phenyl-C₁-C₄-alkyl” refers to alkyl having 1 to 4 carbon atoms(as defined above), wherein one hydrogen atom of the alkyl radical isreplaced by a phenyl radical.

The term “C₃-C₆-cycloalkyl” refers to monocyclic saturated hydrocarbonradicals having 3 to 8 carbon ring members such as cyclopropyl (C₃H₅),cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.

The terms “C(═O)—(C₁-C₄-alkyl) or C(═O)—(C₁-C₄-alkoxy)” refer to aradical which is attached through the carbon atom of the —C(═O)— groupas indicated by the number valence of the carbon atom.

The term “aliphatic” refers to compounds or radicals composed of carbonand hydrogen and which are non-aromatic compounds. An “alicyclic”compound or radical is an organic compound that is both aliphatic andcyclic. They contain one or more all-carbon rings which may be eithersaturated or unsaturated, but do not have aromatic character.

The terms “cyclic moiety” or “cyclic group” refer to a radical which isan alicyclic ring or an aromatic ring, such as, for example, phenyl orheteroaryl.

The term “and wherein any of the aliphatic or cyclic groups areunsubstituted or substituted with . . . ” refers to aliphatic groups,cyclic groups and groups, which contain an aliphatic and a cyclic moietyin one group, such as in, for example, C₃-C₈-cycloalkyl-C₁-C₄-alkyl;therefore a group which contains an aliphatic and a cyclic moiety bothof these moieties may be substituted or unsubstituted independently ofeach other.

The term “phenyl” refers to an aromatic ring systems including sixcarbon atoms (commonly referred to as benzene ring.

The term “saturated 3- to 7-membered carbocycle” is to be understood asmeaning monocyclic saturated carbocycles having 3, 4 or 5 carbon ringmembers. Examples include cyclopropyl, cyclopentyl, cyclohexyl,cycloheptyl, and the like.

The term “saturated 3- to 6-membered heterocycle, wherein the saturatedheterocycle includes besides carbon atoms further 1, 2 or 3 heteroatomsselected from N, O and S as ring member atoms”, is to be understood asmeaning monocyclic heterocycles, for example: a 3- or 4-memberedsaturated heterocycle which contains 1 or 2 heteroatoms from the groupconsisting of N, O and S as ring members, such as oxirane, aziridine,thiirane, oxetane, azetidine, thiethane, [1,2]dioxetane,[1,2]dithietane, [1,2]diazetidine;

and a 5-membered saturated heterocycle which contains 1, 2 or 3heteroatoms from the group consisting of N, O and S as ring members suchas 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl,3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl,4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl,4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl,4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl,5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl,2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl,1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl,1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl,1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl,1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl,2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl,2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl,2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl,2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl,2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl,2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl,2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl,2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl,2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl,2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl,2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl,2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl,3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl,3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl,4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl,4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl,2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl,3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl,3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl,2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl,2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl.

In respect of the variables, the embodiments of the intermediatescorrespond to the embodiments of the compounds I. Preference is given tothose compounds I and, where applicable, also to compounds of allsubformulae provided herein, e. g. formulae I.1, I.2, I.1a, I.1b, I.1c,I.A, I.B, I.C, I.D. I.E, I.F, I.G, I.H, I.J and I.K, wherein variablesL, p, R¹, R², R³, R⁴, R^(A) and n have independently of each other ormore preferably in combination (any possible combination of 2 or moresubstituents as defined herein) the following meanings:

In a preferred embodiment R^(A) is independently selected from the groupconsisting of halogen, C₁-C₆-alkyl or C₃-C₈-cycloalkyl. In anotherpreferred embodiment R^(A) is independently selected from the groupconsisting of halogen, methyl or ethyl. More preferably R^(A) isindependently selected from the group consisting of halogen, inparticular R^(A) is fluorine.

In one aspect of the invention n is 0, 1 or 2, preferably n is 0 or 1.In a particularly preferred aspect n is 0.

In one aspect of the invention R¹ is C₁-C₆-alkyl or C₁-C₆-alkoxy; andwherein any of the aliphatic groups are unsubstituted or substitutedwith 1, 2, 3 or up to the maximum possible number of identical ordifferent radicals selected from the group consisting of C₁-C₆-alkoxyand C₃-C₈-cycloalkyl.

In one aspect of the invention R² is hydrogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₂-C₆-alkenyl, ethynyl, propargyl, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkenyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl or phenyl; and whereinany of the aliphatic or cyclic groups are unsubstituted or substitutedwith 1, 2, 3, 4 or up to the maximum possible number of identical ordifferent radicals selected from the group consisting of halogen, cyano,C₁-C₆-alkyl and C₁-C₆-alkoxy; more preferably from halogen, inparticular the radical is fluorine.

In another aspect R² is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, propargyl,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkenyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl orphenyl; and wherein any of the aliphatic or cyclic groups areunsubstituted or substituted with 1, 2, 3, 4 or up to the maximumpossible number of identical or different radicals selected from thegroup consisting of halogen, cyano, C₁-C₆-alkyl and C₁-C₆-alkoxy; morepreferably from halogen, in particular the radical is fluorine.

In a preferred aspect of the invention R² is hydrogen, C₁-C₆-alkyl,C₁-C₆-alkenyl, propargyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkylor phenyl; and wherein any of the aliphatic or cyclic groups areunsubstituted or substituted with 1, 2, 3, 4 or up to the maximumpossible number of identical or different radicals selected from thegroup consisting of halogen or C₁-C₆-alkyl, in particular fluorine.

In another aspect R² is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, propargyl,C₃-C₈-cycloalkyl or C₃-C₈-cycloalkyl-C₁-C₄-alkyl.

In a further aspect R² is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl orpropargyl.

In yet another aspect R² is hydrogen, methyl, ethyl, iso-propyl,cyclopropyl, cyclopropyl-CH₂—, allyl, phenyl, 4-F-phenyl or 2-F-phenyl.

In a more preferred aspect of the invention R² is hydrogen, methyl,ethyl, n-propyl, iso-propyl, cyclopropyl, cyclopropyl-CH₂— or allyl.

In a particularly preferred aspect R² is hydrogen, methy or ethyl.

In a further aspect R² is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₃-C₈-cycloalkyl or C₃-C₈-cycloalkyl-C₁-C₄-alkyl; in particularhydrogen, methyl, ethyl, iso-propyl, cyclopropyl, cyclopropyl-CH₂— orallyl; more particularly hydrogen, methyl or ethyl; and R¹ isC₁-C₆-alkyl or C₁-C₆-alkoxy; and wherein any of the above-mentionedaliphatic or cyclic groups are unsubstituted or substituted with 1, 2, 3or up to the maximum possible number of identical or different radicalsselected from the group consisting of hydroxy, cyano, C₁-C₆-alkyl andC₁-C₆-alkoxy.

In yet another embodiment R² is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl orC₃-C₈-cycloalkyl; in particular hydrogen, methyl, ethyl, iso-propyl,cyclopropyl, cyclopropyl-CH₂— or allyl; more particularly hydrogen,methyl or ethyl; and R¹ is C₁-C₆-alkyl or C₁-C₆-alkoxy; and wherein thealiphatic groups in R¹ are unsubstituted or substituted with 1, 2, 3, 4or up to the maximum possible number of identical or different radicalsselected from the group consisting of C₁-C₆-alkyl and C₁-C₆-alkoxy.

In a preferred aspect of the invention R² is hydrogen, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₃-C₈-cycloalkyl or C₃-C₈-cycloalkyl-C₁-C₄-alkyl; inparticular hydrogen, methyl, ethyl, iso-propyl, cyclopropyl,cyclopropyl-CH₂— or allyl; more particularly hydrogen, methyl or ethyl;and R¹ is C₁-C₆-alkyl or C₁-C₆-alkoxy; and wherein the alkyl group in R¹is substituted with 1, 2, 3, 4, 5 or up to the maximum possible numberof identical or different halogen atoms; and wherein the alkyl group isfurther unsubstituted or substituted with 1, 2, 3 or up to the maximumpossible number of identical or different groups selected from the groupconsisting of C₁-C₆-alkyl or C₃-C₈-cycloalkyl.

In a further embodiment R² is hydrogen, C₁-C₆-alkyl, C₁-C₆-alkenyl,C₃-C₈-cycloalkyl or C₃-C₈-cycloalkyl-C₁-C₄-alkyl; preferably hydrogen,methyl, ethyl, iso-propyl, cyclopropyl, cyclopropyl-CH₂— or allyl; andR¹ is C₁-C₆-alkyl; and wherein the alkyl group in R¹ is furtherunsubstituted or substituted with 1, 2, 3 or up to the maximum possiblenumber of identical or different groups selected from the groupconsisting of C₁-C₆-alkyl or C₃-C₈-cycloalkyl.

In one embodiment the invention relates to compounds of the formula I,wherein R³ and R⁴ independently of each other are hydrogen, halogen,C₁-C₆-alkyl or C₁-C₆-haloalkyl; with the exception of compounds of theformula I wherein R³ and R⁴ both are hydrogen.

In another embodiment the invention relates to compounds of the formulaI, wherein R³ and R⁴ independently of each other are hydrogen orC₁-C₄-alkyl; preferably hydrogen, methyl or ethyl; with the exception ofcompounds of the formula I wherein R³ and R⁴ both are hydrogen.

In a further embodiment R³ and R⁴ are independently of each otherhydrogen, fluorine, methyl or trifluoromethyl; with the exception ofcompounds of the formula I wherein R³ and R⁴ both are hydrogen.

In another aspect R³ and R⁴ are both hydrogen.

In a further aspect R³ is hydrogen and R⁴ is methyl.

In a further aspect R³ is hydrogen and R⁴ is trifluoromethyl.

In a further aspect R³ is hydrogen and R⁴ is difluoromethyl.

In a further aspect R³ is hydrogen and R⁴ is trichloromethyl.

In a further aspect R³ is hydrogen and R⁴ is dichloromethyl.

In yet another aspect R³ and R⁴ are both methyl.

In a further aspect R³ and R⁴ are both fluorine.

In one embodiment R³ and R⁴ are both trifluoromethyl.

In one embodiment R³ and R⁴ together with the carbon atom to which theyare bound form a vinyl group or a saturated monocyclic 3- to 5-memberedsaturated heterocycle or saturated carbocycle; and wherein the saturatedheterocycle includes beside one or more carbon atoms no heteroatoms or 1or 2 heteroatoms independently selected from N, O and S as ring memberatoms; and wherein the vinyl group, the heterocycle or the carbocycle isunsubstituted or substituted 1, 2, 3, 4 or up to the maximum possiblenumber of identical or different radicals selected from the groupconsisting of halogen, cyano and C₁-C₂-alkyl.

In another embodiment R³ and R⁴ together with the carbon atom to whichthey are bound form a vinyl group or a 3- or 4-membered carbocylic ring;and wherein the vinyl group or the carbocylic ring is unsubstituted.

In another aspect R³ and R⁴ together with the carbon atom to which theyare bound form a vinyl group or a cyclopropyl group, wherein the vinylgroup or the cyclopropyl group is unsubstituted.

In another aspect R³ and R⁴ together with the carbon atom to which theyare bound form a cyclopropyl ring, wherein the cyclopropyl ring isunsubstituted.

In still another embodiment R³ and R⁴ together with the carbon atom towhich they are bound form a saturated 3-membered heterocycle; whereinthe heterocycle includes beside two carbon atoms one heteroatom selectedfrom N, O and S as ring member atoms; and wherein the heterocycle isunsubstituted.

In one embodiment the invention relates to compounds of the formula I.1or to compounds of the formula I.2, or the N-oxides, or theagriculturally acceptable salts thereof

wherein n is 0 or 1, and wherein the meaning of the variables L, R^(A),R¹, R², R³, R⁴ are as defined or preferably defined herein for compoundsof the formula I.

Another embodiment of the invention relates to compounds of the formulaeI.1 or I.2, wherein n is 0; L is —C(═S)—; R³ and R⁴ are independentlyselected from hydrogen, halogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl; or R³and R⁴ together with the carbon atom to which they are bound form acyclopropyl ring; and wherein R¹ and R² are as defined or preferablydefined herein; with the exception of compounds of the formula I whereinR³ and R⁴ both are hydrogen.

Another embodiment of the invention relates to compounds of the formulaeI.1 or I.2, wherein n is 0; L is —SO₂—; R³ and R⁴ are independentlyselected from hydrogen, halogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl; or R³and R⁴ together with the carbon atom to which they are bound form acyclopropyl ring; and wherein R¹ and R² are as defined or preferablydefined herein; with the exception of compounds of the formula I whereinR³ and R⁴ both are hydrogen.

Another embodiment of the invention relates to compounds of the formulaeI.1 or I.2, wherein n is 0; L is —C(═S)—; R³ and R⁴ are independentlyselected from hydrogen, methyl or trifluoromethyl; and wherein R¹ and R²are as defined or preferably defined herein; with the exception ofcompounds of the formula I wherein R³ and R⁴ both are hydrogen.

Another embodiment of the invention relates to compounds of the formulaeI.1 or I.2, wherein n is 0; L is —SO₂—; R³ and R⁴ are independentlyselected from hydrogen, methyl or trifluoromethyl; and wherein R¹ and R²are as defined or preferably defined herein; with the exception ofcompounds of the formula I wherein R³ and R⁴ both are hydrogen.

In a further embodiment the invention relates to compounds I.1a offormula I.1, or the N-oxides, or the agriculturally acceptable saltsthereof, wherein:

-   R^(A) is independently selected from the group consisting of    halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and    C₁-C₆-haloalkoxy;-   n is 0 or 1;-   L is —(C═S)— or —S(═O)₂—;-   R¹ is C₁-C₆-alkyl or C₁-C₆-alkoxy; and wherein any of the aliphatic    groups is unsubstituted or substituted with 1, 2, 3 or up to the    maximum possible number of identical or different radicals selected    from the group consisting of hydroxy, cyano, C₁-C₆-alkyl and    C₁-C₆-alkoxy;-   R² is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, propargyl,    C₃-C₈-cycloalkyl or C₃-C₈-cycloalkyl-C₁-C₄-alkyl;-   R³, R⁴ independently of each other are hydrogen, halogen, cyano,    C₁-C₆-alkyl or C₁-C₆-haloalkyl; or-   R³ and R⁴ together with the carbon atom to which they are bound form    a vinyl group or a saturated monocyclic 3- to 5-membered heterocycle    or carbocycle, wherein the heterocycle includes beside carbon atoms    1 or 2 heteroatoms independently selected from N, O and S as ring    member atoms; and wherein the vinyl group, the heterocycle or the    carbocycle is unsubstituted or substituted with 1, 2, 3, 4 or up to    the maximum possible number of identical or different radicals    selected from the group consisting of halogen, cyano and    C₁-C₂-alkyl; with the exception of compounds of the formula I    wherein R³ and R⁴ both are hydrogen.

In a further embodiment the invention relates to compounds I.1a, whereinn is 0, and wherein R³ and R⁴ are independently selected from hydrogen,halogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl; or R³ and R⁴ together with thecarbon atom to which they are bound form a cyclopropyl ring; with theexception of compounds of the formula I wherein R³ and R⁴ both arehydrogen.

In a further embodiment the invention relates to compounds I.1b offormula I.1, or the N-oxides, or the agriculturally acceptable saltsthereof, wherein:

-   R^(A) is independently selected from the group consisting of    halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and    C₁-C₆-haloalkoxy;-   n is 0 or 1;-   L is —(C═S)— or —S(═O)₂—;-   R¹ is C₁-C₆-alkyl;-   R² is hydrogen, methyl, ethyl, n-propyl, iso-propyl, cyclopropyl,    cyclopropyl-CH₂— or allyl;-   R³, R⁴ independently of each other are hydrogen, halogen, cyano,    C₁-C₆-alkyl or C₁-C₆-haloalkyl; or-   R³ and R⁴ together with the carbon atom to which they are bound form    a vinyl group or a saturated monocyclic 3- to 5-membered heterocycle    or carbocycle, wherein the heterocycle includes beside carbon atoms    1 or 2 heteroatoms independently selected from N, O and S as ring    member atoms; and wherein the vinyl group, the heterocycle or the    carbocycle is unsubstituted or substituted with 1, 2, 3, 4 or up to    the maximum possible number of identical or different radicals    selected from the group consisting of halogen, cyano and    C₁-C₂-alkyl; with the exception of compounds of the formula I    wherein R³ and R⁴ both are hydrogen.

In a further embodiment the invention relates to compounds I.1b, whereinn is 0, and wherein R³ and R⁴ are independently selected from hydrogen,halogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl; or R³ and R⁴ together with thecarbon atom to which they are bound form a cyclopropyl ring; with theexception of compounds of the formula I wherein R³ and R⁴ both arehydrogen.

In a further embodiment the invention relates to compounds I.1c offormula I.1, or the N-oxides, or the agriculturally acceptable saltsthereof, wherein:

-   n is 0;-   L is —(C═S)— or —S(═O)₂—;-   R¹ is C₁-C₆-alkyl;-   R² is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, propargyl,    C₃-C₈-cycloalkyl or C₃-C₈-cycloalkyl-C₁-C₄-alkyl;-   R³, R⁴ independently of each other are hydrogen, methyl or    trifluoromethyl; or R³ and R⁴ together with the carbon atom to which    they are bound form a cyclopropyl ring; with the exception of    compounds of the formula I wherein R³ and R⁴ both are hydrogen.

In a further embodiment the invention relates to compounds I.1c, whereinR² is hydrogen, methyl, ethyl, n-propyl, iso-propyl, cyclopropyl,cyclopropyl-CH₂— or allyl; and wherein R³ and R⁴ are independentlyselected from hydrogen, halogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl; or R³and R⁴ together with the carbon atom to which they are bound form acyclopropyl ring; with the exception of compounds of the formula Iwherein R³ and R⁴ both are hydrogen.

According to one embodiment, the present invention relates to compoundsof the formulae I.A, I.B, I.C, I.D. I.E, I.F, I.G, I.H, I.J and I.K andto their use for controlling phytopathogenic fungi, wherein thevariables R¹ and R² in compounds I.A, I.B, I.C, I.D. I.E, I.F, I.G, I.H,I.J and I.K are as defined or preferably defined herein.

Preference is given to compounds of the formula I, which are compiled inTables 1 to 10 below, and which may be used according to the invention.

Table 1: Compounds of the formula I.A, in which R¹ and R² for eachindividual compound corresponds in each case to one line A-1 to A-593 ofTable A (compounds I.A.A-1 to I.A.A-593).

This means, for example, that a compound of formula I.A, wherein R¹ is2,2,2-trifluoroethyl and R² is hydrogen (corresponding to the definitionA-4 in Table A) is named I.A.A-4.

Table 2: Compounds of the formula I.B, in which R¹ and R² for eachindividual compound corresponds in each case to one line A-1 to A-593 ofTable A (compounds I.B.A-1 to I.B.A-593).

This means, for example, that a compound of formula I.B, wherein R¹ istrifluoromethyl and R² is methyl (corresponding to the definition A-18in Table A) is named I.B.A-18.

Table 3: Compounds of the formula I.C, in which R¹ and R² for eachindividual compound corresponds in each case to one line A-1 to A-593 ofTable A (compounds I.C.A-1 to I.C.A-593) Table 4: Compounds of theformula I.D, in which R¹ and R² for each individual compound correspondsin each case to one line A-1 to A-593 of Table A (compounds I.D.A-1 toI.D.A-593).

Table 5: Compounds of the formula I.E, in which R¹ and R² for eachindividual compound corresponds in each case to one line A-1 to A-593 ofTable A (compounds I.E.A-1 to I.E.A-593).

Table 6: Compounds of the formula I.F, in which R¹ and R² for eachindividual compound corresponds in each case to one line A-1 to A-593 ofTable A (compounds I.F.A-1 to I.F.A-593).

Table 7: Compounds of the formula I.G, in which R¹ and R² for eachindividual compound corresponds in each case to one line A-1 to A-593 ofTable A (compounds I.G.A-1 to I.G.A-593).

Table 8: Compounds of the formula I.H, in which R¹ and R² for eachindividual compound corresponds in each case to one line A-1 to A-593 ofTable A (compounds I.H.A-1 to I.H.A-593)

Table 9: Compounds of the formula I.J, in which R¹ and R² for eachindividual compound corresponds in each case to one line A-1 to A-593 ofTable A (compounds I.J.A-1 to I.J.A-593).

Table 10: Compounds of the formula I.K, in which R¹ and R² for eachindividual compound corresponds in each case to one line A-1 to A-593 ofTable A (compounds I.K.A-1 to I.K.A-593).

TABLE A No. R¹ R² A-1  CH₃ hydrogen A-2  CH₂CH₃ hydrogen A-3  CH₂CH₂CH₃hydrogen A-4  CH(CH₃)₂ hydrogen A-5  CH₂CH₂CH₂CH₃ hydrogen A-6 CH(CH₃)CH₂CH₃ hydrogen A-7  CH₂CH(CH₃)CH₃ hydrogen A-8  CH(CH₂CH₃)₂hydrogen A-9  C(CH₃)₃ hydrogen A-10  OCH₃ hydrogen A-11  OCH₂CH₃hydrogen A-12  OCH₂CH₂CH₃ hydrogen A-13  OCH(CH₃)₂ hydrogen A-14 OCH₂CH₂CH₂CH₃ hydrogen A-15  OCH(CH₃)CH₂CH₃ hydrogen A-16 OCH₂CH(CH₃)CH₃ hydrogen A-17  OC(CH₃)₃ hydrogen A-18  difluoromethylhydrogen A-19  trifluoromethyl hydrogen A-20  2,2-difluoroethyl hydrogenA-21  2,2,2-trifluoroethyl hydrogen A-22  2-chloro-2- hydrogenfluoroethyl A-23  2-chloro-2,2- hydrogen difluoroethyl A-24 2,2,2-trichloroethyl hydrogen A-25  pentafluoroethyl hydrogen A-26 3,3,3- hydrogen trifluoropropyl A-27  CH₂CF₂CF₃ hydrogen A-28  CF₂CF₂CF₃hydrogen A-29  CH(CH₃)CF₃ hydrogen A-30  CH₂CF₂CH₃ hydrogen A-31 CH₂C(CH₃)₂F hydrogen A-32  CH₂CH(CH₃)CF₃ hydrogen A-33  CH₂C(CH₃)₂CF₃hydrogen A-34  CH₃ methyl A-35  CH₂CH₃ methyl A-36  CH₂CH₂CH₃ methylA-37  CH (CH₃)₂ methyl A-38  CH(CH₂CH₃)₂ methyl A-39  CH₂CH₂CH₂CH₃methyl A-40  CH(CH₃)CH₂CH₃ methyl A-41  CH₂CH(CH₃)CH₃ methyl A-42 C(CH₃)₃ methyl A-43  OCH₃ methyl A-44  OCH₂CH₃ methyl A-45  OCH₂CH₂CH₃methyl A-46  OCH(CH₃)₂ methyl A-47  OCH₂CH₂CH₂CH₃ methyl A-48 OCH(CH₃)CH₂CH₃ methyl A-49  OCH₂CH(CH₃)CH₃ methyl A-50  OC(CH₃)₃ methylA-51  difluoromethyl methyl A-52  trifluoromethyl methyl A-53 2,2-difluoroethyl methyl A-54  2,2,2-trifluoroethyl methyl A-55 2-chloro-2- methyl fluoroethyl A-56  2-chloro-2,2- methyl difluoroethylA-57  2,2,2-trichloroethyl methyl A-58  pentafluoroethyl methyl A-59 3,3,3- methyl trifluoropropyl A-60  CH₂CF₂CF₃ methyl A-61  CF₂CF₂CF₃methyl A-62  CH(CH₃)CF₃ methyl A-63  CH₂CF₂CH₃ methyl A-64  CH₂C(CH₃)₂Fmethyl A-65  CH₂CH(CH₃)CF₃ methyl A-66  CH₂C(CH₃)₂CF₃ methyl A-67  CH₃ethyl A-68  CH₂CH₃ ethyl A-69  CH₂CH₂CH₃ ethyl A-70  CH(CH₃)₂ ethylA-71  CH₂CH₂CH₂CH₃ ethyl A-72  CH(CH₃)CH₂CH₃ ethyl A-73  CH₂CH(CH₃)CH₃ethyl A-74  CH(CH₂CH₃)₂ ethyl A-75  C(CH₃)₃ ethyl A-76  OCH₃ ethyl A-77 OCH₂CH₃ ethyl A-78  OCH₂CH₂CH₃ ethyl A-79  OCH(CH₃)₂ ethyl A-80 OCH₂CH₂CH₂CH₃ ethyl A-81  OCH(CH₃)CH₂CH₃ ethyl A-82  OCH₂CH(CH₃)CH₃ethyl A-83  OC(CH₃)₃ ethyl A-84  difluoromethyl ethyl A-85 trifluoromethyl ethyl A-86  2,2-difluoroethyl ethyl A-87 2,2,2-trifluoroethyl ethyl A-88  2-chloro-2- ethyl fluoroethyl A-89 2-chloro-2,2- ethyl difluoroethyl A-90  2,2,2-trichloroethyl ethyl A-91 pentafluoroethyl ethyl A-92  3,3,3- ethyl trifluoropropyl A-93 CH₂CF₂CF₃ ethyl A-94  CF₂CF₂CF₃ ethyl A-95  CH(CH₃)CF₃ ethyl A-96 CH₂CF₂CH₃ ethyl A-97  CH₂C(CH₃)₂F ethyl A-98  CH₂CH(CH₃)CF₃ ethyl A-99 CH₂C(CH₃)₂CF₃ ethyl A-100 CH₃ n-propyl A-101 CH₂CH₃ n-propyl A-102CH₂CH₂CH₃ n-propyl A-103 CH(CH₃)₂ n-propyl A-104 CH₂CH₂CH₂CH₃ n-propylA-105 CH(CH₃)CH₂CH₃ n-propyl A-106 CH₂CH(CH₃)CH₃ n-propyl A-107CH(CH₂CH₃)₂ n-propyl A-108 C(CH₃)₃ n-propyl A-109 OCH₃ n-propyl A-110OCH₂CH₃ n-propyl A-111 OCH₂CH₂CH₃ n-propyl A-112 OCH(CH₃)₂ n-propylA-113 OCH₂CH₂CH₂CH₃ n-propyl A-114 OCH(CH₃)CH₂CH₃ n-propyl A-115OCH₂CH(CH₃)CH₃ n-propyl A-116 OC(CH₃)₃ n-propyl A-117 difluoromethyln-propyl A-118 trifluoromethyl n-propyl A-119 2,2-difluoroethyl n-propylA-120 2,2,2-trifluoroethyl n-propyl A-121 2-chloro-2- n-propylfluoroethyl A-122 2-chloro-2,2- n-propyl difluoroethyl A-1232,2,2-trichloroethyl n-propyl A-124 pentafluoroethyl n-propyl A-1253,3,3- n-propyl trifluoropropyl A-126 CH₂CF₂CF₃ n-propyl A-127 CF₂CF₂CF₃n-propyl A-128 CH(CH₃)CF₃ n-propyl A-129 CH₂CF₂CH₃ n-propyl A-130CH₂C(CH₃)₂F n-propyl A-131 CH₂CH(CH₃)CF₃ n-propyl A-132 CH₂C(CH₃)₂CF₃n-propyl A-133 CH₃ vinyl A-134 CH₂CH₃ vinyl A-135 CH₂CH₂CH₃ vinyl A-136CH(CH₃)₂ vinyl A-137 CH₂CH₂CH₂CH₃ vinyl A-138 CH(CH₃)CH₂CH₃ vinyl A-139CH₂CH(CH₃)CH₃ vinyl A-140 C(CH₃)₃ vinyl A-141 CH(CH₂CH₃)₂ vinyl A-142OCH₃ vinyl A-143 OCH₂CH₃ vinyl A-144 OCH₂CH₂CH₃ vinyl A-145 OCH(CH₃)₂vinyl A-146 OCH₂CH₂CH₂CH₃ vinyl A-147 OCH(CH₃)CH₂CH₃ vinyl A-148OCH₂CH(CH₃)CH₃ vinyl A-149 OC(CH₃)₃ vinyl A-150 difluoromethyl vinylA-151 trifluoromethyl vinyl A-152 2,2-difluoroethyl vinyl A-1532,2,2-trifluoroethyl vinyl A-154 2-chloro-2- vinyl fluoroethyl A-1552-chloro-2,2- vinyl difluoroethyl A-156 2,2,2-trichloroethyl vinyl A-157pentafluoroethyl vinyl A-158 3,3,3- vinyl trifluoropropyl A-159CH₂CF₂CF₃ vinyl A-160 CF₂CF₂CF₃ vinyl A-161 CH(CH₃)CF₃ vinyl A-162CH₂CF₂CH₃ vinyl A-163 CH₂C(CH₃)₂F vinyl A-164 CH₂CH(CH₃)CF₃ vinyl A-165CH₂C(CH₃)₂CF₃ vinyl A-166 CH₃ tert-butyl A-167 CH₂CH₃ tert-butyl A-168CH₂CH₂CH₃ tert-butyl A-169 CH(CH₃)₂ tert-butyl A-170 CH₂CH₂CH₂CH₃tert-butyl A-171 CH(CH₃)CH₂CH₃ tert-butyl A-172 CH₂CH(CH₃)CH₃ tert-butylA-173 CH(CH₂CH₃)₂ tert-butyl A-174 C(CH₃)₃ tert-butyl A-175 OCH₃tert-butyl A-176 OCH₂CH₃ tert-butyl A-177 OCH₂CH₂CH₃ tert-butyl A-178OCH(CH₃)₂ tert-butyl A-179 OCH₂CH₂CH₂CH₃ tert-butyl A-180 OCH(CH₃)CH₂CH₃tert-butyl A-181 OCH₂CH(CH₃)CH₃ tert-butyl A-182 OC(CH₃)₃ tert-butylA-183 difluoromethyl tert-butyl A-184 trifluoromethyl tert-butyl A-1852,2-difluoroethyl tert-butyl A-186 2,2,2-trifluoroethyl tert-butyl A-1872-chloro-2- tert-butyl fluoroethyl A-188 2-chloro-2,2- tert-butyldifluoroethyl A-189 2,2,2-trichloroethyl tert-butyl A-190pentafluoroethyl tert-butyl A-191 3,3,3- tert-butyl trifluoropropylA-192 CH₂CF₂CF₃ tert-butyl A-193 CF₂CF₂CF₃ tert-butyl A-194 CH(CH₃)CF₃tert-butyl A-195 CH₂CF₂CH₃ tert-butyl A-196 CH₂C(CH₃)₂F tert-butyl A-197CH₂CH(CH₃)CF₃ tert-butyl A-198 CH₂C(CH₃)₂CF₃ tert-butyl A-199 CH₃iso-propyl A-200 CH₂CH₃ iso-propyl A-201 CH₂CH₂CH₃ iso-propyl A-202CH(CH₃)₂ iso-propyl A-203 CH₂CH₂CH₂CH₃ iso-propyl A-204 CH(CH₃)CH₂CH₃iso-propyl A-205 CH₂CH(CH₃)CH₃ iso-propyl A-206 CH(CH₂CH₃)₂ iso-propylA-207 C(CH₃)₃ iso-propyl A-208 OCH₃ iso-propyl A-209 OCH₂CH₃ iso-propylA-210 OCH₂CH₂CH₃ iso-propyl A-211 OCH(CH₃)₂ iso-propyl A-212OCH₂CH₂CH₂CH₃ iso-propyl A-213 OCH(CH₃)CH₂CH₃ iso-propyl A-214OCH₂CH(CH₃)CH₃ iso-propyl A-215 OC(CH₃)₃ iso-propyl A-216 difluoromethyliso-propyl A-217 trifluoromethyl iso-propyl A-218 2,2-difluoroethyliso-propyl A-219 2,2,2-trifluoroethyl iso-propyl A-220 2-chloro-2-iso-propyl fluoroethyl A-221 2-chloro-2,2- iso-propyl difluoroethylA-222 2,2,2-trichloroethyl iso-propyl A-223 pentafluoroethyl iso-propylA-224 3,3,3- iso-propyl trifluoropropyl A-225 CH₂CF₂CF₃ iso-propyl A-226CF₂CF₂CF₃ iso-propyl A-227 CH(CH₃)CF₃ iso-propyl A-228 CH₂CF₂CH₃iso-propyl A-229 CH₂C(CH₃)₂F iso-propyl A-230 CH₂CH(CH₃)CF₃ iso-propylA-231 CH₂C(CH₃)₂CF₃ iso-propyl A-232 CH₃ cyclopropyl A-233 CH₂CH₃cyclopropyl A-234 CH₂CH₂CH₃ cyclopropyl A-235 CH(CH₃)₂ cyclopropyl A-236CH₂CH₂CH₂CH₃ cyclopropyl A-237 CH(CH₃)CH₂CH₃ cyclopropyl A-238CH₂CH(CH₃)CH₃ cyclopropyl A-239 CH(CH₂CH₃)₂ cyclopropyl A-240 C(CH₃)₃cyclopropyl A-241 OCH₃ cyclopropyl A-242 OCH₂CH₃ cyclopropyl A-243OCH₂CH₂CH₃ cyclopropyl A-244 OCH(CH₃)₂ cyclopropyl A-245 OCH₂CH₂CH₂CH₃cyclopropyl A-246 OCH(CH₃)CH₂CH₃ cyclopropyl A-247 OCH₂CH(CH₃)CH₃cyclopropyl A-248 OC(CH₃)₃ cyclopropyl A-249 difluoromethyl cyclopropylA-250 trifluoromethyl cyclopropyl A-251 2,2-difluoroethyl cyclopropylA-252 2,2,2-trifluoroethyl cyclopropyl A-253 2-chloro-2- cyclopropylfluoroethyl A-254 2-chloro-2,2- cyclopropyl difluoroethyl A-2552,2,2-trichloroethyl cyclopropyl A-256 pentafluoroethyl cyclopropylA-257 3,3,3- cyclopropyl trifluoropropyl A-258 CH₂CF₂CF₃ cyclopropylA-259 CF₂CF₂CF₃ cyclopropyl A-260 CH(CH₃)CF₃ cyclopropyl A-261 CH₂CF₂CH₃cyclopropyl A-262 CH₂C(CH₃)₂F cyclopropyl A-263 CH₂CH(CH₃)CF₃cyclopropyl A-264 CH₂C(CH₃)₂CF₃ cyclopropyl A-265 CH₃ cyclobutyl A-266CH₂CH₃ cyclobutyl A-267 CH₂CH₂CH₃ cyclobutyl A-268 CH(CH₃)₂ cyclobutylA-269 CH₂CH₂CH₂CH₃ cyclobutyl A-270 CH(CH₃)CH₂CH₃ cyclobutyl A-271CH₂CH(CH₃)CH₃ cyclobutyl A-272 CH(CH₂CH₃)₂ cyclobutyl A-273 C(CH₃)₃cyclobutyl A-274 OCH₃ cyclobutyl A-275 OCH₂CH₃ cyclobutyl A-276OCH₂CH₂CH₃ cyclobutyl A-277 OCH(CH₃)₂ cyclobutyl A-278 OCH₂CH₂CH₂CH₃cyclobutyl A-279 OCH(CH₃)CH₂CH₃ cyclobutyl A-280 OCH₂CH(CH₃)CH₃cyclobutyl A-281 OC(CH₃)₃ cyclobutyl A-282 difluoromethyl cyclobutylA-283 trifluoromethyl cyclobutyl A-284 2,2-difluoroethyl cyclobutylA-285 2,2,2-trifluoroethyl cyclobutyl A-286 2-chloro-2- cyclobutylfluoroethyl A-287 2-chloro-2,2- cyclobutyl difluoroethyl A-2882,2,2-trichloroethyl cyclobutyl A-289 pentafluoroethyl cyclobutyl A-2903,3,3- cyclobutyl trifluoropropyl A-291 CH₂CF₂CF₃ cyclobutyl A-292CF₂CF₂CF₃ cyclobutyl A-293 CH(CH₃)CF₃ cyclobutyl A-294 CH₂CF₂CH₃cyclobutyl A-295 CH₂C(CH₃)₂F cyclobutyl A-296 CH₂CH(CH₃)CF₃ cyclobutylA-297 CH₂C(CH₃)₂CF₃ cyclobutyl A-298 CH₃ cyclopentyl A-299 CH₂CH₃cyclopentyl A-300 CH₂CH₂CH₃ cyclopentyl A-301 CH(CH₃)₂ cyclopentyl A-302CH₂CH₂CH₂CH₃ cyclopentyl A-303 CH(CH₃)CH₂CH₃ cyclopentyl A-304CH₂CH(CH₃)CH₃ cyclopentyl A-305 CH(CH₂CH₃)₂ cyclopentyl A-306 C(CH₃)₃cyclopentyl A-307 OCH₃ cyclopentyl A-308 OCH₂CH₃ cyclopentyl A-309OCH₂CH₂CH₃ cyclopentyl A-310 OCH(CH₃)₂ cyclopentyl A-311 OCH₂CH₂CH₂CH₃cyclopentyl A-312 OCH(CH₃)CH₂CH₃ cyclopentyl A-313 OCH₂CH(CH₃)CH₃cyclopentyl A-314 OC(CH₃)₃ cyclopentyl A-315 difluoromethyl cyclopentylA-316 trifluoromethyl cyclopentyl A-317 2,2-difluoroethyl cyclopentylA-318 2,2,2-trifluoroethyl cyclopentyl A-319 2-chloro-2- cyclopentylfluoroethyl A-320 2-chloro-2,2- cyclopentyl difluoroethyl A-3212,2,2-trichloroethyl cyclopentyl A-322 pentafluoroethyl cyclopentylA-323 3,3,3- cyclopentyl trifluoropropyl A-324 CH₂CF₂CF₃ cyclobutylA-325 CF₂CF₂CF₃ cyclopentyl A-326 CH(CH₃)CF₃ cyclopentyl A-327 CH₂CF₂CH₃cyclopentyl A-328 CH₂C(CH₃)₂F cyclopentyl A-329 CH₂CH(CH₃)CF₃cyclopentyl A-330 CH₂C(CH₃)₂CF₃ cyclopentyl A-331 CH₃ cyclohexyl A-332CH₂CH₃ cyclohexyl A-333 CH₂CH₂CH₃ cyclohexyl A-334 CH(CH₃)₂ cyclohexylA-335 CH₂CH₂CH₂CH₃ cyclohexyl A-336 CH(CH₃)CH₂CH₃ cyclohexyl A-337CH₂CH(CH₃)CH₃ cyclohexyl A-338 CH(CH₂CH₃)₂ cyclohexyl A-339 C(CH₃)₃cyclohexyl A-340 OCH₃ cyclohexyl A-341 OCH₂CH₃ cyclohexyl A-342OCH₂CH₂CH₃ cyclohexyl A-343 OCH(CH₃)₂ cyclohexyl A-344 OCH₂CH₂CH₂CH₃cyclohexyl A-345 OCH(CH₃)CH₂CH₃ cyclohexyl A-346 OCH₂CH(CH₃)CH₃cyclohexyl A-347 OC(CH₃)₃ cyclohexyl A-348 difluoromethyl cyclohexylA-349 trifluoromethyl cyclohexyl A-350 2,2-difluoroethyl cyclohexylA-351 2,2,2-trifluoroethyl cyclohexyl A-352 2-chloro-2- cyclohexylfluoroethyl A-353 2-chloro-2,2- cyclohexyl difluoroethyl A-3542,2,2-trichloroethyl cyclohexyl A-355 pentafluoroethyl cyclohexyl A-3563,3,3- cyclohexyl trifluoropropyl A-357 CH₂CF₂CF₃ cyclohexyl A-358CF₂CF₂CF₃ cyclohexyl A-359 CH(CH₃)CF₃ cyclohexyl A-360 CH₂CF₂CH₃cyclohexyl A-361 CH₂C(CH₃)₂F cyclohexyl A-362 CH₂CH(CH₃)CF₃ cyclohexylA-363 CH₂C(CH₃)₂CF₃ cyclohexyl A-364 CH₃ allyl A-365 CH₂CH₃ allyl A-366CH₂CH₂CH₃ allyl A-367 CH(CH₃)₂ allyl A-368 CH₂CH₂CH₂CH₃ allyl A-369CH(CH₃)CH₂CH₃ allyl A-370 CH₂CH(CH₃)CH₃ allyl A-371 CH(CH₂CH₃)₂ allylA-372 C(CH₃)₃ allyl A-373 OCH₃ allyl A-374 OCH₂CH₃ allyl A-375OCH₂CH₂CH₃ allyl A-376 OCH(CH₃)₂ allyl A-377 OCH₂CH₂CH₂CH₃ allyl A-378OCH(CH₃)CH₂CH₃ allyl A-379 OCH₂CH(CH₃)CH₃ allyl A-380 OC(CH₃)₃ allylA-381 difluoromethyl allyl A-382 trifluoromethyl allyl A-3832,2-difluoroethyl allyl A-384 2,2,2-trifluoroethyl allyl A-3852-chloro-2- allyl fluoroethyl A-386 2-chloro-2,2- allyl difluoroethylA-387 2,2,2-trichloroethyl allyl A-388 pentafluoroethyl allyl A-3893,3,3- allyl trifluoropropyl A-390 CH₂CF₂CF₃ allyl A-391 CF₂CF₂CF₃ allylA-392 CH(CH₃)CF₃ allyl A-393 CH₂CF₂CH₃ allyl A-394 CH₂C(CH₃)₂F allylA-395 CH₂CH(CH₃)CF₃ allyl A-396 CH₂C(CH₃)₂CF₃ allyl A-397 CH₃ phenylA-398 CH₂CH₃ phenyl A-399 CH₂CH₂CH₃ phenyl A-400 CH(CH₃)₂ phenyl A-401CH₂CH₂CH₂CH₃ phenyl A-402 CH(CH₃)CH₂CH₃ phenyl A-403 CH₂CH(CH₃)CH₃phenyl A-404 CH(CH₂CH₃)₂ phenyl A-405 C(CH₃)₃ phenyl A-406 OCH₃ phenylA-407 OCH₂CH₃ phenyl A-408 OCH₂CH₂CH₃ phenyl A-409 OCH(CH₃)₂ phenylA-410 OCH₂CH₂CH₂CH₃ phenyl A-411 OCH(CH₃)CH₂CH₃ phenyl A-412OCH₂CH(CH₃)CH₃ phenyl A-413 OC(CH₃)₃ phenyl A-414 difluoromethyl phenylA-415 trifluoromethyl phenyl A-416 2,2-difluoroethyl phenyl A-4172,2,2-trifluoroethyl phenyl A-418 2-chloro-2- phenyl fluoroethyl A-4192-chloro-2,2- phenyl difluoroethyl A-420 2,2,2-trichloroethyl phenylA-421 pentafluoroethyl phenyl A-422 3,3,3- phenyl trifluoropropyl A-423CH₂CF₂CF₃ phenyl A-424 CF₂CF₂CF₃ phenyl A-425 CH(CH₃)CF₃ phenyl A-426CH₂CF₂CH₃ phenyl A-427 CH₂C(CH₃)₂F phenyl A-428 CH₂CH(CH₃)CF₃ phenylA-429 CH₂C(CH₃)₂CF₃ phenyl A-430 CH₃ 4-fluoro- phenyl A-431 CH₂CH₃4-fluoro- phenyl A-432 CH₂CH₂CH₃ 4-fluoro- phenyl A-433 CH(CH₃)₂4-fluoro- phenyl A-434 CH₂CH₂CH₂CH₃ 4-fluoro- phenyl A-435 CH(CH₃)CH₂CH₃4-fluoro- phenyl A-436 CH₂CH(CH₃)CH₃ 4-fluoro- phenyl A-437 CH(CH₂CH₃)₂4-fluoro- phenyl A-438 C(CH₃)₃ 4-fluoro- phenyl A-439 OCH₃ 4-fluoro-phenyl A-440 OCH₂CH₃ 4-fluoro- phenyl A-441 OCH₂CH₂CH₃ 4-fluoro- phenylA-442 OCH(CH₃)₂ 4-fluoro- phenyl A-443 OCH₂CH₂CH₂CH₃ 4-fluoro- phenylA-444 OCH(CH₃)CH₂CH₃ 4-fluoro- phenyl A-445 OCH₂CH(CH₃)CH₃ 4-fluoro-phenyl A-446 OC(CH₃)₃ 4-fluoro- phenyl A-447 difluoromethyl 4-fluoro-phenyl A-448 trifluoromethyl 4-fluoro- phenyl A-449 2,2-difluoroethyl4-fluoro- phenyl A-450 2,2,2-trifluoroethyl 4-fluoro- phenyl A-4512-chloro-2- 4-fluoro- fluoroethyl phenyl A-452 2-chloro-2,2- 4-fluoro-difluoroethyl phenyl A-453 2,2,2-trichloroethyl 4-fluoro- phenyl A-454pentafluoroethyl 4-fluoro- phenyl A-455 3,3,3- 4-fluoro- trifluoropropylphenyl A-456 CH₂CF₂CF₃ 4-fluoro- phenyl A-457 CF₂CF₂CF₃ 4-fluoro- phenylA-458 CH(CH₃)CF₃ 4-fluoro- phenyl A-459 CH₂CF₂CH₃ 4-fluoro- phenyl A-460CH₂C(CH₃)₂F 4-fluoro- phenyl A-461 CH₂CH(CH₃)CF₃ 4-fluoro- phenyl A-462CH₂C(CH₃)₂CF₃ 4-fluoro- phenyl A-463 CH₃ 2-fluoro- phenyl A-464 CH₂CH₃2-fluoro- phenyl A-465 CH₂CH₂CH₃ 2-fluoro- phenyl A-466 CH(CH₃)₂2-fluoro- phenyl A-467 CH₂CH₂CH₂CH₃ 2-fluoro- phenyl A-468 CH(CH₃)CH₂CH₃2-fluoro- phenyl A-469 CH₂CH(CH₃)CH₃ 2-fluoro- phenyl A-470 CH(CH₂CH₃)₂2-fluoro- phenyl A-471 C(CH₃)₃ 2-fluoro- phenyl A-472 OCH₃ 2-fluoro-phenyl A-473 OCH₂CH₃ 2-fluoro- phenyl A-474 OCH₂CH₂CH₃ 2-fluoro- phenylA-475 OCH(CH₃)₂ 2-fluoro- phenyl A-476 OCH₂CH₂CH₂CH₃ 2-fluoro- phenylA-477 OCH(CH₃)CH₂CH₃ 2-fluoro- phenyl A-478 OCH₂CH(CH₃)CH₃ 2-fluoro-phenyl A-479 OC(CH₃)₃ 2-fluoro- phenyl A-480 difluoromethyl 2-fluoro-phenyl A-481 trifluoromethyl 2-fluoro- phenyl A-482 2,2-difluoroethyl2-fluoro- phenyl A-483 2,2,2-trifluoroethyl 2-fluoro- phenyl A-4842-chloro-2- 2-fluoro- fluoroethyl phenyl A-485 2-chloro-2,2- 2-fluoro-difluoroethyl phenyl A-486 2,2,2-trichloroethyl 2-fluoro- phenyl A-487pentafluoroethyl 2-fluoro- phenyl A-488 3,3,3- 2-fluoro- trifluoropropylphenyl A-489 CH₂CF₂CF₃ 2-fluoro- phenyl A-490 CF₂CF₂CF₃ 2-fluoro- phenylA-491 CH(CH₃)CF₃ 2-fluoro- phenyl A-492 CH₂CF₂CH₃ 2-fluoro-phenyl A-493CH₂C(CH₃)₂F 2-fluoro-phenyl A-494 CH₂CH(CH₃)CF₃ 2-fluoro-phenyl A-495CH₂C(CH₃)₂CF₃ 2-fluoro-phenyl A-496 CH₃ 2,4-difluoro- phenyl A-497CH₂CH₃ 2,4-difluoro- phenyl A-498 CH₂CH₂CH₃ 2,4-difluoro- phenyl A-499CH(CH₃)₂ 2,4-difluoro- phenyl A-500 CH₂CH₂CH₂CH₃ 2,4-difluoro- phenylA-501 CH(CH₃)CH₂CH₃ 2,4-difluoro- phenyl A-502 CH₂CH(CH₃)CH₃2,4-difluoro- phenyl A-503 CH(CH₂CH₃)₂ 2,4-difluoro- phenyl A-504C(CH₃)₃ 2,4-difluoro- phenyl A-505 OCH₃ 2,4-difluoro- phenyl A-506OCH₂CH₃ 2,4-difluoro- phenyl A-507 OCH₂CH₂CH₃ 2,4-difluoro- phenyl A-508OCH(CH₃)₂ 2,4-difluoro- phenyl A-509 OCH₂CH₂CH₂CH₃ 2,4-difluoro- phenylA-510 OCH(CH₃)CH₂CH₃ 2,4-difluoro- phenyl A-511 OCH₂CH(CH₃)CH₃2,4-difluoro- phenyl A-512 OC(CH₃)₃ 2,4-difluoro- phenyl A-513difluoromethyl 2,4-difluoro- phenyl A-514 trifluoromethyl 2,4-difluoro-phenyl A-515 2,2-difluoroethyl 2,4-difluoro- phenyl A-5162,2,2-trifluoroethyl 2,4-difluoro- phenyl A-517 2-chloro-2-2,4-difluoro- fluoroethyl phenyl A-518 2-chloro-2,2- 2,4-difluoro-difluoroethyl phenyl A-519 2,2,2-trichloroethyl 2,4-difluoro- phenylA-520 pentafluoroethyl 2,4-difluoro- phenyl A-521 3,3,3- 2,4-difluoro-trifluoropropyl phenyl A-522 CH₂CF₂CF₃ 2,4-difluoro- phenyl A-523CF₂CF₂CF₃ 2,4-difluoro- phenyl A-524 CH(CH₃)CF₃ 2,4-difluoro- phenylA-525 CH₂CF₂CH₃ 2,4-difluoro- phenyl A-526 CH₂C(CH₃)₂F 2,4-difluoro-phenyl A-527 CH₂CH(CH₃)CF₃ 2,4-difluoro- phenyl A-528 CH₂C(CH₃)₂CF₃2,4-difluoro- phenyl A-529 CH₃ propargyl A-530 CH₂CH₃ propargyl A-531CH₂CH₂CH₃ propargyl A-532 CH(CH₃)₂ propargyl A-533 CH₂CH₂CH₂CH₃propargyl A-534 CH(CH₃)CH₂CH₃ propargyl A-535 CH₂CH(CH₃)CH₃ propargylA-536 CH(CH₂CH₃)₂ propargyl A-537 C(CH₃)₃ propargyl A-538 OCH₃ propargylA-539 OCH₂CH₃ propargyl A-540 OCH₂CH₂CH₃ propargyl A-541 OCH(CH₃)₂propargyl A-542 OCH₂CH₂CH₂CH₃ propargyl A-543 OCH(CH₃)CH₂CH₃ propargylA-544 OCH₂CH(CH₃)CH₃ propargyl A-545 OC(CH₃)₃ propargyl A-546difluoromethyl propargyl A-547 trifluoromethyl propargyl A-5482,2-difluoroethyl propargyl A-549 2,2,2-trifluoroethyl propargyl A-5502-chloro-2- propargyl fluoroethyl A-551 2-chloro-2,2- propargyldifluoroethyl A-552 2,2,2-trichloroethyl propargyl A-553pentafluoroethyl propargyl A-554 3,3,3- propargyl trifluoropropyl A-555CH₂CF₂CF₃ propargyl A-556 CF₂CF₂CF₃ propargyl A-557 CH(CH₃)CF₃ propargylA-558 CH₂CF₂CH₃ propargyl A-559 CH₂C(CH₃)₂F propargyl A-560CH₂CH(CH₃)CF₃ propargyl A-561 CH₂C(CH₃)₂CF₃ propargyl A-562 CH₃cyclopropyl- CH2- A-563 CH₂CH₃ cyclopropyl- CH²⁻ A-564 CH₂CH₂CH₃cyclopropyl- CH²⁻ A-565 CH(CH₃)₂ cyclopropyl- CH²⁻ A-566 CH₂CH₂CH₂CH₃cyclopropyl- CH²⁻ A-567 CH(CH₃)CH₂CH₃ cyclopropyl- CH²⁻ A-568CH₂CH(CH₃)CH₃ cyclopropyl- CH²⁻ A-569 CH(CH₂CH₃)₂ cyclopropyl- CH²⁻A-570 C(CH₃)₃ cyclopropyl- CH²⁻ A-571 OCH₃ cyclopropyl- CH²⁻ A-572OCH₂CH₃ cyclopropyl- CH²⁻ A-573 OCH₂CH₂CH₃ cyclopropyl- CH²⁻ A-574OCH(CH₃)₂ cyclopropyl- CH²⁻ A-575 OCH₂CH₂CH₂CH₃ cyclopropyl- CH²⁻ A-576OCH(CH₃)CH₂CH₃ cyclopropyl- CH²⁻ A-577 OCH₂CH(CH₃)CH₃ cyclopropyl- CH²⁻A-578 OC(CH₃)₃ cyclopropyl- CH²⁻ A-579 difluoromethyl cyclopropyl- CH²⁻A-580 trifluoromethyl cyclopropyl- CH²⁻ A-581 2,2-difluoroethylcyclopropyl- CH²⁻ A-582 2,2,2-trifluoroethyl cyclopropyl- CH²⁻ A-5832-chloro-2- cyclopropyl- fluoroethyl CH²⁻ A-584 2-chloro-2,2-cyclopropyl- difluoroethyl CH²⁻ A-585 2,2,2-trichloroethyl cyclopropyl-CH²⁻ A-586 pentafluoroethyl cyclopropyl- CH²⁻ A-587 3,3,3- cyclopropyl-trifluoropropyl CH²⁻ A-588 CH₂CF₂CF₃ cyclopropyl- CH²⁻ A-589 CF₂CF₂CF₃cyclopropyl- CH²⁻ A-590 CH(CH₃)CF₃ cyclopropyl- CH²⁻ A-591 CH₂CF₂CH₃cyclopropyl- CH²⁻ A-592 CH₂C(CH₃)₂F cyclopropyl- CH²⁻ A-593CH₂CH(CH₃)CF₃ cyclopropyl- CH²⁻

The compounds of the formula I can be prepared according to methods orin analogy to methods that are described in the prior art. The synthesistakes advantage of starting materials that are commercially available ormay be prepared according to conventional procedures starting fromreadily available compounds. For example, compounds of the formula Iwherein L is —(C═S)— can be prepared in two steps by reacting ofoxadiazole amine II with compounds of type Ilia (for example aceticchloride or anhydride, LG=chlorine or acetate) in an organic solvent andin the presence of a base followed by thionylation of the obtainedcarboxamide with either Lawesson's reagent or diphosphorus pentasulfide,as previously described (see, for example, Journal of Organic Chemistry,2008, 73, 9102 or European Journal of Organic Chemistry; 2015, 30,6687).

Compounds of formula I wherein L is —S(═O)_(p)— can be prepared byreacting compounds of the formula II in the presence of a base withcompounds of the formula IIIb wherein LG is preferably chlorine.

Compounds of the formula II can be prepared by reacting amidoximes oftype IV with trifluoroacetic anhydride in an organic solvent, preferablyan ethereal solvent at temperatures between 0° C. and 100° C.,preferably at room temperature, as previously described in WO2013/008162 or EP 276432.

A skilled person will recognize that compounds of type IV can beaccessed by treating nitriles of type V with hydroxylamine (or itshydrochloric acid salt) in an organic solvent and in the presence of abase (for precedents see for example WO 2009/074950, WO 2006/013104).Preferably ethanol and potassium carbonate. If appropriate, water may beadded to enhance solubility of the reactants. The reaction is bestperformed at elevated temperatures, most preferably in the range between60° C. and 80° C.

Compounds V are either commercially available or can be accessed fromreadily available starting materials through methods that are known to aperson skilled in the art.

An alternative synthesis route to obtain compounds of formula I startsfrom a compound of the formula V, which is reacted with compounds IIIaor IIIb as described above. The resulting sulfonamide or carboxamidecompounds VI still bears the cyano group, which is subsequentlyconverted into the oxadiazole ring to produce compounds of the formula Ivia a two step cyclization reaction with hydroxylamine hydrochloride andtrifluoroacetic anhydride as described above. The carboxamide mayfurther be thionylated as described above.

The compounds of the formula I or compositions comprising said compoundsaccording to the invention and the mixtures comprising said compoundsand compositions, respectively, are suitable as fungicides. They aredistinguished by an outstanding effectiveness against a broad spectrumof phytopathogenic fungi, including soil-borne fungi, which deriveespecially from the following classes or are closely related to any ofthem: Ascomycota (Ascomycetes), for example, but not limited to thegenus Cochliobolus, Colletotrichum, Fusarium, Microdochium, Penicillium,Phoma, Magnaporthe, Zymoseptoria, and Pseudocercosporella; Basidiomycota(Basidiomycetes), for example, but not limited to the genus Phakospora,Puccinia, Rhizoctonia, Sphacelotheca, Tilletia, Typhula, and Ustilago;Chytridiomycota (Chytridiomycetes), for example, but not limited to thegenus Chytridiales, and Synchytrium; Deuteromycetes (syn. Fungiimperfecti), for example, but not limited to the genus Ascochyta,Dlodia, Erysiphe, Fusarium, Phomopsis, and Pyrenophora;Peronosporomycetes (syn. Oomycetes), for example but not limited to thegenus Peronospora, Pythium, Phytophthora; Plasmodiophoromycetes, forexample but not limited to the genus Plasmodiophora; Zygomycetes, forexample, but not limited to the genus Rhizopus.

Some of the compounds of the formula I and the compositions according tothe invention are systemically effective and they can be used in cropprotection as foliar fungicides, fungicides for seed dressing and soilfungicides. Moreover, they are suitable for controlling harmful fungi,which inter alia occur in wood or roots of plants.

The compounds I and the compositions according to the invention areparticularly important in the control of a multitude of phytopathogenicfungi on various cultivated plants, such as cereals, e. g. wheat, rye,barley, triticale, oats or rice; beet, e. g. sugar beet or fodder beet;fruits, such as pomes, stone fruits or soft fruits, e. g. apples, pears,plums, peaches, almonds, cherries, strawberries, raspberries,blackberries or gooseberries; leguminous plants, such as lentils, peas,alfalfa or soybeans; oil plants, such as rape, mustard, olives,sunflowers, coconut, cocoa beans, castor oil plants, oil palms, groundnuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiberplants, such as cotton, flax, hemp or jute; citrus fruit, such asoranges, lemons, grapefruits or mandarins; vegetables, such as spinach,lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes,cucurbits or paprika; lauraceous plants, such as avocados, cinnamon orcamphor; energy and raw material plants, such as corn, soybean, rape,sugar cane or oil palm; corn; tobacco; nuts; coffee; tea; bananas; vines(table grapes and grape juice grape vines); hop; turf; sweet leaf (alsocalled Stevia); natural rubber plants or ornamental and forestry plants,such as flowers, shrubs, broad-leaved trees or evergreens, e. g.conifers; and on the plant propagation material, such as seeds, and thecrop material of these plants. Preferably, compounds I and compositionsthereof, respectively are used for controlling a multitude of fungi onfield crops, such as potatoes sugar beets, tobacco, wheat, rye, barley,oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee orsugar cane; fruits; vines; ornamentals; or vegetables, such ascucumbers, tomatoes, beans or squashes.

The term “plant propagation material” is to be understood to denote allthe generative parts of the plant such as seeds and vegetative plantmaterial such as cuttings and tubers (e. g. potatoes), which can be usedfor the multiplication of the plant. This includes seeds, roots, fruits,tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants,including seedlings and young plants, which are to be transplanted aftergermination or after emergence from soil.

These young plants may also be protected before transplantation by atotal or partial treatment by immersion or pouring.

Preferably, treatment of plant propagation materials with compounds Iand compositions thereof, respectively, is used for controlling amultitude of fungi on cereals, such as wheat, rye, barley and oats;rice, corn, cotton and soybeans.

The term “cultivated plants” is to be understood as including plantswhich have been modified by mutagenesis or genetic engineering in orderto provide a new trait to a plant or to modify an already present trait.Mutagenesis includes techniques of random mutagenesis using X-rays ormutagenic chemicals, but also techniques of targeted mutagenesis, tocreate mutations at a specific locus of a plant genome. Targetedmutagenesis techniques frequently use oligonucleotides or proteins likeCRISPR/Cas, zinc-finger nucleases, TALENs or mega-nucleases to achievethe targeting effect. Genetic engineering usually uses recombinant DNAtechniques to create modifications in a plant genome which under naturalcircumstances cannot readily be obtained by cross breeding, mutagenesisor natural recombination. Typically, one or more genes are integratedinto the genome of a plant to add a trait or improve a trait. Theseintegrated genes are also referred to as transgenes in the art, whileplant comprising such transgenes are referred to as transgenic plants.The process of plant transformation usually produces severaltransformation events, which differ in the genomic locus in which atransgene has been integrated. Plants comprising a specific transgene ona specific genomic locus are usually described as comprising a specific“event”, which is referred to by a specific event name. Traits whichhave been introduced in plants or have been modified include herbicidetolerance, insect resistance, increased yield and tolerance to abioticconditions, like drought.

Herbicide tolerance has been created by using mutagenesis as well asusing genetic engineering. Plants which have been rendered tolerant toacetolactate synthase (ALS) inhibitor herbicides by mutagenesis andbreeding comprise plant varieties commercially available under the nameClearfield®.

Herbicide tolerance has been created via the use of transgenes toglyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides, likebromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitors and4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, like isoxaflutoleand mesotrione.

Transgenes which have been used to provide herbicide tolerance traitscomprise: for tolerance to glyphosate: cp4 epsps, epsps grg23ace5,mepsps, 2mepsps, gat4601, gat4621, goxv247; for tolerance toglufosinate: pat and bar, for tolerance to 2,4-D: aad-1, aad-12; fortolerance to dicamba: dmo; for tolerance to oxynil herbicies: bxn; fortolerance to sulfonylurea herbicides: zm-hra, csr1-2, gm-hra, S4-HrA;for tolerance to ALS inhibitors: csr1-2; and for tolerance to HPPDinhibitors: hppdPF, W336, avhppd-03.

Transgenic corn events comprising herbicide tolerance genes include, butare not limited to, DAS40278, MON801, MON802, MON809, MON810, MON832,MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHG0JG,HCEM485, VCO-Ø1981-5, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10,Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 andTC6275.

Transgenic soybean events comprising herbicide tolerance genes include,but are not limited to, GTS 40-3-2, MON87705, MON87708, MON87712,MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043,DAS44406-6, DAS68416-4, DAS-81419-2, GU262, SYHTØH2, W62, W98, FG72 andCV127.

Transgenic cotton events comprising herbicide tolerance genes include,but are not limited to, 19-51a, 31707, 42317, 81910, 281-24-236,3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698,MON88701, MON88913,GHB119,GHB614, LLCotton25, T303-3 and T304-40.

Transgenic canola events comprising herbicide tolerance genes are forexample, but not excluding others, MON88302, HCR-1, HCN10, HCN28, HCN92,MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2 and RF3.

Insect resistance has mainly been created by transferring bacterialgenes for insecticidal proteins to plants: Transgenes which have mostfrequently been used are toxin genes of Bacillus spp. and syntheticvariants thereof, like cry1A, cry1Ab, cry1Ab-Ac, cry1Ac, cry1A.105,cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1, cry34Ab1,cry35Ab1, cry9C, vip3A(a), vip3Aa20. However, also genes of plantorigin, such as genes coding for protease inhibitors, like CpTI andpinII, have been transferred to other plants. A further approach usestransgenes such as dvsnf7 to produce double-stranded RNA in plants.

Transgenic corn events comprising genes for insecticidal proteins ordouble stranded RNA include, but are not limited to, Bt10, Bt11, Bt176,MON801, MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034,33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418 andMZIR098. Transgenic soybean events comprising genes for insecticidalproteins include, but are not limited to, MON87701, MON87751 andDAS-81419. Transgenic cotton events comprising genes for insecticidalproteins include, but are not limited to, SGK321, MON531, MON757,MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601, Event1,COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236,3006-210-23, GHB119 and SGK321.

Increased yield has been created by using the transgene athb17, beingpresent for example in corn event MON87403, or by using the transgenebbx32, being present for example in the soybean event MON87712.

Cultivated plants comprising a modified oil content have been created byusing the transgenes: gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A and fatb1-A.Soybean events comprising at least one of these genes are: 260-05,MON87705 and MON87769.

Tolerance to abiotic conditions, such as drought, has been created byusing the transgene cspB, comprised by the corn event MON87460 and byusing the transgene Hahb-4, comprised by soybean event IND-ØØ41Ø-5.

Traits are frequently combined by combining genes in a transformationevent or by combining different events during the breeding processresulting in a cultivated plant with stacked traits. Preferredcombinations of traits are combinations of herbicide tolerance traits todifferent groups of herbicides, combinations of insect tolerance todifferent kind of insects, in particular tolerance to lepidopteran andcoleopteran insects, combinations of herbicide tolerance with one orseveral types of insect resistance, combinations of herbicide tolerancewith increased yield as well as combinations of herbicide tolerance andtolerance to abiotic conditions.

Plants comprising singular or stacked traits as well as the genes andevents providing these traits are well known in the art. For example,detailed information as to the mutagenized or integrated genes and therespective events are available from websites of the organizations“International Service for the Acquisition of Agri-biotech Applications(ISAAA)” (http://www.isaaa.org/gmapprovaldatabase) and the “Center forEnvironmental Risk Assessment (CERA)”(http://cera-gmc.org/GMCropDatabase). Further information on specificevents and methods to detect them can be found for canola events MS1,MS8, RF3, GT73, MON88302, KK179 in WO01/031042, WO01/041558,WO01/041558, WO02/036831, WO11/153186, WO13/003558, for cotton eventsMON1445, MON15985, MON531 (MON15985), LLCotton25, MON88913, COT102,281-24-236, 3006-210-23, COT67B, GHB614, T304-40, GHB119, MON88701,81910 in WO02/034946, WO02/100163, WO02/100163, WO03/013224,WO04/072235, WO04/039986, WO05/103266, WO05/103266, WO06/128573,WO07/017186, WO08/122406, WO08/151780, WO12/134808, WO13/112527; forcorn events GA21, MON810, DLL25, TC1507, MON863, MIR604, LY038,MON88017, 3272, 59122, NK603, MIR162, MON89034, 98140, 32138, MON87460,5307, 4114, MON87427, DAS40278, MON87411, 33121, MON87403, MON87419 inWO98/044140, U.S. Ser. No. 02/102,582, U.S. Ser. No. 03/126,634,WO04/099447, WO04/011601, WO05/103301, WO05/061720, WO05/059103,WO06/098952, WO06/039376, US2007/292854, WO07/142840, WO07/140256,WO08/112019, WO09/103049, WO09/111263, WO10/077816, WO11/084621,WO11/062904, WO11/022469, WO13/169923, WO14/116854, WO15/053998,WO15/142571; for potato events E12, F10, J3, J55, V11, X17, Y9 inWO14/178910, WO14/178913, WO14/178941, WO14/179276, WO16/183445,WO17/062831, WO17/062825; for rice events LLRICE06, LLRICE601, LLRICE62in WO00/026345, WO00/026356, WO00/026345; and for soybean events H7-1,MON89788, A2704-12, A5547-127, DP305423, DP356043, MON87701, MON87769,CV127, MON87705, DAS68416-4, MON87708, MON87712, SYHT0H2, DAS81419,DAS81419×DAS44406-6, MON87751 in WO04/074492, WO06/130436, WO06/108674,WO06/108675, WO08/054747, WO08/002872, WO09/064652, WO09/102873,WO10/080829, WO10/037016, WO11/066384, WO11/034704, WO12/051199,WO12/082548, WO13/016527, WO13/016516, WO14/201235.

The use of compounds I and compositions according to the invention,respectively, on cultivated plants may result in effects which arespecific to a cultivated plant comprising a certain gene or event. Theseeffects might involve changes in growth behavior or changed resistanceto biotic or abiotic stress factors. Such effects may in particularcomprise enhanced yield, enhanced resistance or tolerance to insects,nematodes, fungal, bacterial, Mycoplasma, viral or viroid pathogens aswell as early vigour, early or delayed ripening, cold or heat toleranceas well as changed amino acid or fatty acid spectrum or content.

The compounds I and compositions thereof, respectively, are particularlysuitable for controlling the following plant diseases:

Albugo spp. (white rust) on ornamentals, vegetables (e. g. A. candida)and sunflowers (e. g. A. tragopogonis); Alternaria spp. (Alternaria leafspot) on vegetables, rape (A. brassicola or brassicae), sugar beets (A.tenuis), fruits, rice, soybeans, potatoes (e. g. A. solani or A.alternata), tomatoes (e. g. A. solani or A. alternata) and wheat;Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. oncereals and vegetables, e. g. A. tritici (anthracnose) on wheat and A.hordei on barley; Bipolaris and Drechslera spp. (teleomorph:Cochliobolus spp.), e. g. Southern leaf blight (D. maydis) or Northernleaf blight (B. zeicola) on corn, e. g. spot blotch (B. sorokiniana) oncereals and e. g. B. oryzae on rice and turfs; Blumeria (formerlyErysiphe) graminis (powdery mildew) on cereals (e. g. on wheat orbarley); Botrytis cinerea (teleomorph: Botryotinia fuckeliana: greymold) on fruits and berries (e. g. strawberries), vegetables (e. g.lettuce, carrots, celery and cabbages), rape, flowers, vines, forestryplants and wheat; Bremia lactucae (downy mildew) on lettuce;Ceratocystis (syn. Ophiostoma) spp. (rot or wilt) on broad-leaved treesand evergreens, e. g. C. ulmi (Dutch elm disease) on elms; Cercosporaspp. (Cercospora leaf spots) on corn (e. g. Gray leaf spot: C.zeae-maydis), rice, sugar beets (e. g. C. beticola), sugar cane,vegetables, coffee, soybeans (e. g. C. sojina or C. kikuchi) and rice;Cladosporium spp. on tomatoes (e. g. C. fulvum: leaf mold) and cereals,e. g. C. herbarum (black ear) on wheat; Claviceps purpurea (ergot) oncereals; Cochliobolus (anamorph: Helminthosporium of Bipolaris) spp.(leaf spots) on corn (C. carbonum), cereals (e. g. C. sativus, anamorph:B. sorokiniana) and rice (e. g. C. miyabeanus, anamorph: H. oryzae);Colletotrichum (teleomorph: Glomerella) spp. (anthracnose) on cotton (e.g. C. gossypii), corn (e. g. C. graminicola: Anthracnose stalk rot),soft fruits, potatoes (e. g. C. coccodes: black dot), beans (e. g. C.lindemuthianum) and soybeans (e. g. C. truncatum or C. gloeosporioides);Corticium spp., e. g. C. sasakii (sheath blight) on rice; Corynesporacassiicola (leaf spots) on soybeans and ornamentals; Cycloconium spp.,e. g. C. oleaginum on olive trees; Cylindrocarpon spp. (e. g. fruit treecanker or young vine decline, teleomorph: Nectria or Neonectria spp.) onfruit trees, vines (e. g. C. liriodendri, teleomorph: Neonectrialiriodendri: Black Foot Disease) and ornamentals; Dematophora(teleomorph: Rosellinia) necatrix (root and stem rot) on soybeans;Diaporthe spp., e. g. D. phaseolorum (damping off) on soybeans;Drechslera (syn. Helminthosporium, teleomorph: Pyrenophora) spp. oncorn, cereals, such as barley (e. g. D. teres, net blotch) and wheat (e.g. D. tritici-repentis: tan spot), rice and turf; Esca (dieback,apoplexy) on vines, caused by Formitiporia (syn. Phellinus) punctata, F.mediterranea, Phaeomoniella chlamydospora (earlier Phaeoacremoniumchlamydosporum), Phaeoacremonium aleophilum and/or Botryosphaeriaobtusa; Elsinoe spp. on pome fruits (E. pyri), soft fruits (E. veneta:anthracnose) and vines (E. ampelina: anthracnose); Entyloma oryzae (leafsmut) on rice; Epicoccum spp. (black mold) on wheat; Erysiphe spp.(powdery mildew) on sugar beets (E. betae), vegetables (e. g. E. pisi),such as cucurbits (e. g. E. cichoracearum), cabbages, rape (e. g. E.cruciferarum); Eutypa lata (Eutypa canker or dieback, anamorph:Cytosporina lata, syn. Libertella blepharis) on fruit trees, vines andornamental woods; Exserohilum (syn. Helminthosporium) spp. on corn (e.g. E. turcicum); Fusarium (teleomorph: Gibberella) spp. (wilt, root orstem rot) on various plants, such as F. graminearum or F. culmorum (rootrot, scab or head blight) on cereals (e. g. wheat or barley), F.oxysporum on tomatoes, F. solani (f. sp. glycines now syn. F.virguliforme) and F. tucumaniae and F. brasilense each causing suddendeath syndrome on soybeans, and F. verticillioides on corn;Gaeumannomyces graminis (take-all) on cereals (e. g. wheat or barley)and corn; Gibberella spp. on cereals (e. g. G. zeae) and rice (e. g. G.fujikuri: Bakanae disease); Glomerella cingulata on vines, pome fruitsand other plants and G. gossypii on cotton; Grain staining complex onrice; Guignardia bidwellii (black rot) on vines; Gymnosporangium spp. onrosaceous plants and junipers, e. g. G. sabinae (rust) on pears;Helminthosporium spp. (syn. Drechslera, teleomorph: Cochliobolus) oncorn, cereals and rice; Hemileia spp., e. g. H. vastatrix (coffee leafrust) on coffee; Isariopsis clavispora (syn. Cladosporium vitis) onvines; Macrophomina phaseolina (syn. phaseoli) (root and stem rot) onsoybeans and cotton; Microdochium (syn. Fusarium) nivale (pink snowmold) on cereals (e. g. wheat or barley); Microsphaera diffusa (powderymildew) on soybeans; Monilinia spp., e. g. M. laxa, M. fructicola and M.fructigena (bloom and twig blight, brown rot) on stone fruits and otherrosaceous plants; Mycosphaerella spp. on cereals, bananas, soft fruitsand ground nuts, such as e. g. M. graminicola (anamorph: Septoriatritici, Septoria blotch) on wheat or M. fijiensis (black Sigatokadisease) on bananas; Peronospora spp. (downy mildew) on cabbage (e. g.P. brassicae), rape (e. g. P. parasitica), onions (e. g. P. destructor),tobacco (P. tabacina) and soybeans (e. g. P. manshurica); Phakopsorapachyrhizi and P. meibomiae (soybean rust) on soybeans; Phialophora spp.e. g. on vines (e. g. P. tracheiphila and P. tetraspora) and soybeans(e. g. P. gregata: stem rot); Phoma lingam (root and stem rot) on rapeand cabbage and P. betae (root rot, leaf spot and damping-off) on sugarbeets; Phomopsis spp. on sunflowers, vines (e. g. P. viticola: can andleaf spot) and soybeans (e. g. stem rot: P. phaseoli, teleomorph:Diaporthe phaseolorum); Physoderma maydis (brown spots) on corn;Phytophthora spp. (wilt, root, leaf, fruit and stem root) on variousplants, such as paprika and cucurbits (e. g. P. capsici), soybeans (e.g. P. megasperma, syn. P. sojae), potatoes and tomatoes (e. g. P.infestans: late blight) and broad-leaved trees (e. g. P. ramorum: suddenoak death); Plasmodiophora brassicae (club root) on cabbage, rape,radish and other plants; Plasmopara spp., e. g. P. viticola (grapevinedowny mildew) on vines and P. halstedii on sunflowers; Podosphaera spp.(powdery mildew) on rosaceous plants, hop, pome and soft fruits, e. g.P. leucotricha on apples; Polymyxa spp., e. g. on cereals, such asbarley and wheat (P. graminis) and sugar beets (P. betae) and therebytransmitted viral diseases; Pseudocercosporella herpotrichoides(eyespot, teleomorph: Tapesia yallundae) on cereals, e. g. wheat orbarley; Pseudoperonospora (downy mildew) on various plants, e. g. P.cubensis on cucurbits or P. humili on hop; Pseudopezicula tracheiphila(red fire disease or ‘rotbrenner’, anamorph: Phialophora) on vines;Puccinia spp. (rusts) on various plants, e. g. P. triticina (brown orleaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarfrust), P. graminis (stem or black rust) or P. recondita (brown or leafrust) on cereals, such as e. g. wheat, barley or rye, P. kuehnii (orangerust) on sugar cane and P. asparagi on asparagus; Pyrenophora (anamorph:Drechslera) tritici-repentis (tan spot) on wheat or P. teres (netblotch) on barley; Pyricularia spp., e. g. P. oryzae (teleomorph:Magnaporthe grisea, rice blast) on rice and P. grisea on turf andcereals; Pythium spp. (damping-off) on turf, rice, corn, wheat, cotton,rape, sunflowers, soybeans, sugar beets, vegetables and various otherplants (e. g. P. ultimum or P. aphanidermatum); Ramularia spp., e. g. R.collo-cygni(Ramularia leaf spots, Physiological leaf spots) on barleyand R. beticola on sugar beets; Rhizoctonia spp. on cotton, rice,potatoes, turf, corn, rape, potatoes, sugar beets, vegetables andvarious other plants, e. g. R. solani (root and stem rot) on soybeans,R. solani (sheath blight) on rice or R. cerealis (Rhizoctonia springblight) on wheat or barley; Rhizopus stolonifer(black mold, soft rot) onstrawberries, carrots, cabbage, vines and tomatoes; Rhynchosporiumsecalis (scald) on barley, rye and triticale; Sarocladium oryzae and S.attenuatum (sheath rot) on rice; Sclerotinia spp. (stem rot or whitemold) on vegetables and field crops, such as rape, sunflowers (e. g. S.sclerotiorum) and soybeans (e. g. S. rolfsii or S. sclerotiorum);Septoria spp. on various plants, e. g. S. glycines (brown spot) onsoybeans, S. tritici(Septoria blotch) on wheat and S. (syn.Stagonospora) nodorum (Stagonospora blotch) on cereals; Uncinula (syn.Erysiphe) necator (powdery mildew, anamorph: Oidium tuckeri) on vines;Setospaeria spp. (leaf blight) on corn (e. g. S. turcicum, syn.Helminthosporium turcicum) and turf; Sphacelotheca spp. (smut) on corn,(e. g. S. reiliana: head smut), sorghum und sugar cane; Sphaerothecafuliginea (powdery mildew) on cucurbits; Spongospora subterranea(powdery scab) on potatoes and thereby transmitted viral diseases;Stagonospora spp. on cereals, e. g. S. nodorum (Stagonospora blotch,teleomorph: Leptosphaeria [syn. Phaeosphaeria] nodorum) on wheat;Synchytrium endobioticum on potatoes (potato wart disease); Taphrinaspp., e. g. T. deformans (leaf curl disease) on peaches and T. pruni(plum pocket) on plums; Thielaviopsis spp. (black root rot) on tobacco,pome fruits, vegetables, soybeans and cotton, e. g. T. basicola (syn.Chalara elegans); Tilletia spp. (common bunt or stinking smut) oncereals, such as e. g. T. tritici (syn. T. caries, wheat bunt) and T.controversa (dwarf bunt) on wheat; Typhula incarnata (grey snow mold) onbarley or wheat; Urocystis spp., e. g. U. occulta (stem smut) on rye;Uromyces spp. (rust) on vegetables, such as beans (e. g. U.appendiculatus, syn. U. phaseoli) and sugar beets (e. g. U. betae);Ustilago spp. (loose smut) on cereals (e. g. U. nuda and U. avaenae),corn (e. g. U. maydis: corn smut) and sugar cane; Venturia spp. (scab)on apples (e. g. V. inaequalis) and pears; and Verticillium spp. (wilt)on various plants, such as fruits and ornamentals, vines, soft fruits,vegetables and field crops, e. g. V. dahliae on strawberries, rape,potatoes and tomatoes.

In a preferred embodiment the compounds I, their mixtures with otheractive compounds as defined herein and compositions thereof,respectively, are particularly suitable for controlling the followingplant diseases: Puccinia spp. (rusts) on various plants, for example,but not limited to P. triticina (brown or leaf rust), P. striiformis(stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem orblack rust) or P. recondita (brown or leaf rust) on cereals, such as e.g. wheat, barley or rye, and Puccinia sorghi (common rust) on maize,Puccinia polysora (southern rust) on maize; and Phakopsoraceae spp. onvarious plants, in particular Phakopsora pachyrhizi and P. meibomiae(soybean rust) on soybeans. The compounds I and compositions thereof,respectively, are also suitable for controlling harmful fungi in theprotection of stored products or harvest and in the protection ofmaterials.

The term “protection of materials” is to be understood to denote theprotection of technical and non-living materials, such as adhesives,glues, wood, paper and paperboard, textiles, leather, paint dispersions,plastics, cooling lubricants, fiber or fabrics, against the infestationand destruction by harmful microorganisms, such as fungi and bacteria.As to the protection of wood and other materials, the particularattention is paid to the following harmful fungi: Ascomycetes such asOphiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophomaspp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp.;Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllumspp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp. andTyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporiumspp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomycesspp. and Zygomycetes such as Mucor spp., and in addition in theprotection of stored products and harvest the following yeast fungi areworthy of note: Candida spp. and Saccharomyces cerevisae.

The method of treatment according to the invention can also be used inthe field of protecting stored products or harvest against attack offungi and microorganisms. According to the present invention, the term“stored products” is understood to denote natural substances of plant oranimal origin and their processed forms, which have been taken from thenatural life cycle and for which long-term protection is desired. Storedproducts of crop plant origin, such as plants or parts thereof, forexample stalks, leafs, tubers, seeds, fruits or grains, can be protectedin the freshly harvested state or in processed form, such as pre-dried,moistened, comminuted, ground, pressed or roasted, which process is alsoknown as post-harvest treatment. Also falling under the definition ofstored products is timber, whether in the form of crude timber, such asconstruction timber, electricity pylons and barriers, or in the form offinished articles, such as furniture or objects made from wood. Storedproducts of animal origin are hides, leather, furs, hairs and the like.The combinations according the present invention can preventdisadvantageous effects such as decay, discoloration or mold. Preferably“stored products” is understood to denote natural substances of plantorigin and their processed forms, more preferably fruits and theirprocessed forms, such as pomes, stone fruits, soft fruits and citrusfruits and their processed forms.

The compounds of formula I can be present in different crystalmodifications whose biological activity may differ. They are likewisesubject matter of the present invention.

The compounds I are employed as such or in form of compositions bytreating the fungi or the plants, plant propagation materials, such asseeds, soil, surfaces, materials or rooms to be protected from fungalattack with a fungicidally effective amount of the active substances.The application can be carried out both before and after the infectionof the plants, plant propagation materials, such as seeds, soil,surfaces, materials or rooms by the fungi.

Plant propagation materials may be treated with compounds I as such or acomposition comprising at least one compound I prophylactically eitherat or before planting or transplanting.

The invention also relates to agrochemical compositions comprising anauxiliary and at least one compound I according to the invention.

An agrochemical composition comprises a fungicidally effective amount ofa compound I. The term “fungicidally effective amount” denotes an amountof the composition or of the compounds I, which is sufficient forcontrolling harmful fungi on cultivated plants or in the protection ofstored products or harvest or of materials and which does not result ina substantial damage to the treated plants, the treated stored productsor harvest, or to the treated materials. Such an amount can vary in abroad range and is dependent on various factors, such as the fungalspecies to be controlled, the treated cultivated plant, stored product,harvest or material, the climatic conditions and the specific compound Iused.

The compounds I, their N-oxides and salts can be converted intocustomary types of agrochemical compositions, e. g. solutions,emulsions, suspensions, dusts, powders, pastes, granules, pressings,capsules, and mixtures thereof. Examples for composition types aresuspensions (e. g. SC, OD, FS), emulsifiable concentrates (e. g. EC),emulsions (e. g. EW, EO, ES, ME), capsules (e. g. CS, ZC), pastes,pastilles, wettable powders or dusts (e. g. WP, SP, WS, DP, DS),pressings (e. g. BR, TB, DT), granules (e. g. WG, SG, GR, FG, GG, MG),insecticidal articles (e. g. LN), as well as gel formulations for thetreatment of plant propagation materials such as seeds (e. g. GF). Theseand further compositions types are defined in the “Catalogue ofpesticide formulation types and international coding system”, TechnicalMonograph No. 2, 6^(th) Ed. May 2008, CropLife International.

The compositions are prepared in a known manner, such as described byMollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001;or by Knowles, New developments in crop protection product formulation,Agrow Reports DS243, T&F Informa, London, 2005.

Suitable auxiliaries are solvents, liquid carriers, solid carriers orfillers, surfactants, dispersants, emulsifiers, wetters, adjuvants,solubilizers, penetration enhancers, protective colloids, adhesionagents, thickeners, humectants, repellents, attractants, feedingstimulants, compatibilizers, bactericides, anti-freezing agents,anti-foaming agents, colorants, tackifiers and binders.

Suitable solvents and liquid carriers are water and organic solvents,such as mineral oil fractions of medium to high boiling point, e. g.kerosene, diesel oil; oils of vegetable or animal origin; aliphatic,cyclic and aromatic hydrocarbons, e. g. toluene, paraffin,tetrahydronaphthalene, alkylated naphthalenes; alcohols, e. g. ethanol,propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones,e. g. cyclohexanone; esters, e. g. lactates, carbonates, fatty acidesters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides,e. g. N-methyl pyrrolidone, fatty acid dimethyl amides; and mixturesthereof. Suitable solid carriers or fillers are mineral earths, e. g.silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays,dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesiumsulfate, magnesium oxide; polysaccharides, e. g. cellulose, starch;fertilizers, e. g. ammonium sulfate, ammonium phosphate, ammoniumnitrate, ureas; products of vegetable origin, e. g. cereal meal, treebark meal, wood meal, nutshell meal, and mixtures thereof. Suitablesurfactants are surface-active compounds, such as anionic, cationic,nonionic and amphoteric surfactants, block polymers, polyelectrolytes,and mixtures thereof. Such surfactants can be used as emulsifier,dispersant, solubilizer, wetter, penetration enhancer, protectivecolloid, or adjuvant. Examples of surfactants are listed inMcCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon'sDirectories, Glen Rock, USA, 2008 (International Ed. or North AmericanEd.).

Suitable anionic surfactants are alkali, alkaline earth or ammoniumsalts of sulfonates, sulfates, phosphates, carboxylates, and mixturesthereof. Examples of sulfonates are alkylaryl sulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates offatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonatesof alkoxylated arylphenols, sulfonates of condensed naphthalenes,sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenesand alkyl naphthalenes, sulfosuccinates or sulfosuccinamates. Examplesof sulfates are sulfates of fatty acids and oils, of ethoxylatedalkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acidesters. Examples of phosphates are phosphate esters. Examples ofcarboxylates are alkyl carboxylates, and carboxylated alcohol oralkylphenol ethoxylates.

Suitable nonionic surfactants are alkoxylates, N-substituted fatty acidamides, amine oxides, esters, sugar-based surfactants, polymericsurfactants, and mixtures thereof. Examples of alkoxylates are compoundssuch as alcohols, alkylphenols, amines, amides, arylphenols, fatty acidsor fatty acid esters which have been alkoxylated with 1 to 50equivalents. Ethylene oxide and/or propylene oxide may be employed forthe alkoxylation, preferably ethylene oxide. Examples of N-substitutedfatty acid amides are fatty acid glucamides or fatty acid alkanolamides.Examples of esters are fatty acid esters, glycerol esters ormonoglycerides. Examples of sugar-based surfactants are sorbitans,ethoxylated sorbitans, sucrose and glucose esters oralkylpolyglucosides. Examples of polymeric surfactants are home- orcopolymers of vinyl pyrrolidone, vinyl alcohols, or vinyl acetate.

Suitable cationic surfactants are quaternary surfactants, for examplequaternary ammonium compounds with one or two hydrophobic groups, orsalts of long-chain primary amines. Suitable amphoteric surfactants arealkylbetains and imidazolines. Suitable block polymers are blockpolymers of the A-B or A-B-A type comprising blocks of polyethyleneoxide and polypropylene oxide, or of the A-B-C type comprising alkanol,polyethylene oxide and polypropylene oxide.

Suitable polyelectrolytes are polyacids or polybases. Examples ofpolyacids are alkali salts of polyacrylic acid or polyacid combpolymers. Examples of polybases are polyvinyl amines or polyethyleneamines.

Suitable adjuvants are compounds, which have a negligible or even nopesticidal activity themselves, and which improve the biologicalperformance of the compound I on the target. Examples are surfactants,mineral or vegetable oils, and other auxiliaries. Further examples arelisted by Knowles, Adjuvants and additives, Agrow Reports DS256, T&FInforma UK, 2006, chapter 5.

Suitable thickeners are polysaccharides (e. g. xanthan gum,carboxymethyl cellulose), inorganic clays (organically modified orunmodified), polycarboxylates, and silicates.

Suitable bactericides are bronopol and isothiazolinone derivatives suchas alkylisothiazolinones and benzisothiazolinones.

Suitable anti-freezing agents are ethylene glycol, propylene glycol,urea and glycerin.

Suitable anti-foaming agents are silicones, long chain alcohols, andsalts of fatty acids.

Suitable colorants (e. g. in red, blue, or green) are pigments of lowwater solubility and water-soluble dyes. Examples are inorganiccolorants (e. g. iron oxide, titan oxide, iron hexacyanoferrate) andorganic colorants (e. g. alizarin-, azo- and phthalocyanine colorants).

Suitable tackifiers or binders are polyvinyl pyrrolidones, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or syntheticwaxes, and cellulose ethers.

Examples for composition types and their preparation are:

i) Water-Soluble Concentrates (SL, LS)

10-60 wt % of a compound I and 5-15 wt % wetting agent (e. g. alcoholalkoxylates) are dissolved in water and/or in a water-soluble solvent(e. g. alcohols) ad 100 wt %. The active substance dissolves upondilution with water.

ii) Dispersible Concentrates (DC)

5-25 wt % of a compound I and 1-10 wt % dispersant (e. g. polyvinylpyrrolidone) are dissolved in organic solvent (e. g. cyclohexanone) ad100 wt %. Dilution with water gives a dispersion.

iii) Emulsifiable Concentrates (EC)

15-70 wt % of a compound I and 5-10 wt % emulsifiers (e. g. calciumdodecylbenzenesulfonate and castor oil ethoxylate) are dissolved inwater-insoluble organic solvent (e. g. aromatic hydrocarbon) ad 100 wt%. Dilution with water gives an emulsion.

iv) Emulsions (EW, EO, ES)

5-40 wt % of a compound I and 1-10 wt % emulsifiers (e. g. calciumdodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in20-40 wt % water-insoluble organic solvent (e. g. aromatic hydrocarbon).This mixture is introduced into water ad 100 wt % by means of anemulsifying machine and made into a homogeneous emulsion. Dilution withwater gives an emulsion.

v) Suspensions (SC, OD, FS)

In an agitated ball mill, 20-60 wt % of a compound I are comminuted withaddition of 2-10 wt % dispersants and wetting agents (e. g. sodiumlignosulfonate and alcohol ethoxylate), 0.1-2 wt % thickener (e. g.xanthan gum) and water ad 100 wt % to give a fine active substancesuspension. Dilution with water gives a stable suspension of the activesubstance. For FS type composition up to 40 wt % binder (e. g. polyvinylalcohol) is added.

vi) Water-Dispersible Granules and Water-Soluble Granules (WG, SG)

50-80 wt % of a compound I are ground finely with addition ofdispersants and wetting agents (e. g. sodium lignosulfonate and alcoholethoxylate) ad 100 wt % and prepared as water-dispersible orwater-soluble granules by means of technical appliances (e. g.extrusion, spray tower, fluidized bed). Dilution with water gives astable dispersion or solution of the active substance.

vii) Water-Dispersible Powders and Water-Soluble Powders (WP, SP, WS)

50-80 wt % of a compound I are ground in a rotor-stator mill withaddition of 1-5 wt % dispersants (e. g. sodium lignosulfonate), 1-3 wt %wetting agents (e. g. alcohol ethoxylate) and solid carrier (e. g.silica gel) ad 100 wt %. Dilution with water gives a stable dispersionor solution of the active substance.

viii) Gel (GW, GF)

In an agitated ball mill, 5-25 wt % of a compound I are comminuted withaddition of 3-10 wt % dispersants (e. g. sodium lignosulfonate), 1-5 wt% thickener (e. g. carboxymethyl cellulose) and water ad 100 wt % togive a fine suspension of the active substance. Dilution with watergives a stable suspension of the active substance.

ix) Microemulsion (ME)

5-20 wt % of a compound I are added to 5-30 wt % organic solvent blend(e. g. fatty acid dimethyl amide and cyclohexanone), 10-25 wt %surfactant blend (e. g. alcohol ethoxylate and arylphenol ethoxylate),and water ad 100%. This mixture is stirred for 1 h to producespontaneously a thermodynamically stable microemulsion.

x) Microcapsules (CS)

An oil phase comprising 5-50 wt % of a compound I, 0-40 wt % waterinsoluble organic solvent (e. g. aromatic hydrocarbon), 2-15 wt %acrylic monomers (e. g. methylmethacrylate, methacrylic acid and a di-or triacrylate) are dispersed into an aqueous solution of a protectivecolloid (e. g. polyvinyl alcohol). Radical polymerization results in theformation of poly(meth)acrylate microcapsules. Alternatively, an oilphase comprising 5-50 wt % of a compound I according to the invention,0-40 wt % water insoluble organic solvent (e. g. aromatic hydrocarbon),and an isocyanate monomer (e. g. diphenylmethene-4,4′-diisocyanatae) aredispersed into an aqueous solution of a protective colloid (e. g.polyvinyl alcohol). The addition of a polyamine (e. g.hexamethylenediamine) results in the formation of polyureamicrocapsules. The monomers amount to 1-10 wt %. The wt % relate to thetotal CS composition.

xi) Dustable Powders (DP, DS)

1-10 wt % of a compound I are ground finely and mixed intimately withsolid carrier (e. g. finely divided kaolin) ad 100 wt %.

xii) Granules (GR, FG)

0.5-30 wt % of a compound I is ground finely and associated with solidcarrier (e. g. silicate) ad 100 wt %. Granulation is achieved byextrusion, spray-drying or fluidized bed.

xiii) Ultra-Low Volume Liquids (UL)

1-50 wt % of a compound I are dissolved in organic solvent (e. g.aromatic hydrocarbon) ad 100 wt %.

The compositions types i) to xiii) may optionally comprise furtherauxiliaries, such as 0.1-1 wt % bactericides, 5-15 wt % anti-freezingagents, 0.1-1 wt % anti-foaming agents, and 0.1-1 wt % colorants.

The agrochemical compositions generally comprise between 0.01 and 95%,preferably between 0.1 and 90%, more preferably between 1 and 70%, andin particular between 10 and 60%, by weight of active substance. Theactive substances are employed in a purity of from 90% to 100%,preferably from 95% to 100% (according to NMR spectrum).

For the purposes of treatment of plant propagation materials,particularly seeds, solutions for seed treatment (LS), Suspoemulsions(SE), flowable concentrates (FS), powders for dry treatment (DS),water-dispersible powders for slurry treatment (WS), water-solublepowders (SS), emulsions (ES), emulsifiable concentrates (EC), and gels(GF) are usually employed. The compositions in question give, aftertwo-to-tenfold dilution, active substance concentrations of from 0.01 to60% by weight, preferably from 0.1 to 40%, in the ready-to-usepreparations. Application can be carried out before or during sowing.Methods for applying compound I and compositions thereof, respectively,onto plant propagation material, especially seeds, include dressing,coating, pelleting, dusting, and soaking as well as in-furrowapplication methods. Preferably, compound I or the compositions thereof,respectively, are applied on to the plant propagation material by amethod such that germination is not induced, e. g. by seed dressing,pelleting, coating and dusting.

When employed in plant protection, the amounts of active substancesapplied are, depending on the kind of effect desired, from 0.001 to 2 kgper ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha.

In treatment of plant propagation materials such as seeds, e. g. bydusting, coating or drenching seed, amounts of active substance of from0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to100 g and most preferably from 5 to 100 g, per 100 kilogram of plantpropagation material (preferably seeds) are generally required.

When used in the protection of materials or stored products, the amountof active substance applied depends on the kind of application area andon the desired effect. Amounts customarily applied in the protection ofmaterials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of activesubstance per cubic meter of treated material.

Various types of oils, wetters, adjuvants, fertilizer, ormicronutrients, and further pesticides (e. g. herbicides, insecticides,fungicides, growth regulators, safeners, biopesticides) may be added tothe active substances or the compositions comprising them as premix or,if appropriate not until immediately prior to use (tank mix). Theseagents can be admixed with the compositions according to the inventionin a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

A pesticide is generally a chemical or biological agent (such aspestidal active ingredient, compound, composition, virus, bacterium,antimicrobial or disinfectant) that through its effect deters,incapacitates, kills or otherwise discourages pests. Target pests caninclude insects, plant pathogens, weeds, mollusks, birds, mammals, fish,nematodes (roundworms), and microbes that destroy property, causenuisance, spread disease or are vectors for disease. The term“pesticide” includes also plant growth regulators that alter theexpected growth, flowering, or reproduction rate of plants; defoliantsthat cause leaves or other foliage to drop from a plant, usually tofacilitate harvest; desiccants that promote drying of living tissues,such as unwanted plant tops; plant activators that activate plantphysiology for defense of against certain pests; safeners that reduceunwanted herbicidal action of pesticides on crop plants; and plantgrowth promoters that affect plant physiology e.g. to increase plantgrowth, biomass, yield or any other quality parameter of the harvestablegoods of a crop plant.

The user applies the composition according to the invention usually froma predosage device, a knapsack sprayer, a spray tank, a spray plane, oran irrigation system. Usually, the agrochemical composition is made upwith water, buffer, and/or further auxiliaries to the desiredapplication concentration and the ready-to-use spray liquor or theagrochemical composition according to the invention is thus obtained.Usually, 20 to 2000 liters, preferably 50 to 400 liters, of theready-to-use spray liquor are applied per hectare of agricultural usefularea.

According to one embodiment, individual components of the compositionaccording to the invention such as parts of a kit or parts of a binaryor ternary mixture may be mixed by the user himself in a spray tank orany other kind of vessel used for applications (e. g. seed treaterdrums, seed pelleting machinery, knapsack sprayer) and furtherauxiliaries may be added, if appropriate.

Consequently, one embodiment of the invention is a kit for preparing ausable pesticidal composition, the kit comprising a) a compositioncomprising component 1) as defined herein and at least one auxiliary;and b) a composition comprising component 2) as defined herein and atleast one auxiliary; and optionally c) a composition comprising at leastone auxiliary and optionally a further active component 3) as definedherein.

Mixing the compounds I or the compositions comprising them in the useform as fungicides with other fungicides results in many cases in anexpansion of the fungicidal spectrum of activity being obtained or in aprevention of fungicide resistance development. Furthermore, in manycases, synergistic effects are obtained.

The following list of pesticides II (e. g. pesticidally-activesubstances and biopesticides), in conjunction with which the compounds Ican be used, is intended to illustrate the possible combinations butdoes not limit them:

A) Respiration Inhibitors

-   -   Inhibitors of complex III at Q_(o) site: azoxystrobin (A.1.1),        coumethoxystrobin (A.1.2), coumoxystrobin (A.1.3), dimoxystrobin        (A.1.4), enestroburin (A.1.5), fenaminstrobin (A.1.6),        fenoxystrobin/flufenoxystrobin (A.1.7), fluoxastrobin (A.1.8),        kresoxim-methyl (A.1.9), mandestrobin (A.1.10), metominostrobin        (A.1.11), orysastrobin (A.1.12), picoxystrobin (A.1.13),        pyraclostrobin (A.1.14), pyrametostrobin (A.1.15),        pyraoxystrobin (A.1.16), trifloxy-strobin (A.1.17),        2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl-acetamide        (A.1.18), pyribencarb (A.1.19), triclopyricarb/chloro-dincarb        (A.1.20), famoxadone (A.1.21), fenamidone (A.1.21a),        methyl-N-[2-[(1,4-dimethyl-5-phenyl-pyrazol-3-yl)oxylmethyl]phenyl]-N-methoxy-carbamate        (A.1.22), metyltetrapole (A.1.25),        (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide        (A.1.34),        (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide        (A.1.35), pyriminostrobin (A.1.36), bifujunzhi (A.1.37),        2-(ortho-((2,5-dimethylphenyl-oxymethylen)phenyl)-3-methoxy-acrylic        acid methylester (A.1.38);    -   inhibitors of complex III at Q; site: cyazofamid (A.2.1),        amisulbrom (A.2.2).        [(6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-di-oxo-1,5-dioxonan-7-yl]        2-methylpropanoate (A.2.3), fenpicoxamid (A.2.4),        florylpicoxamid (A.2.5);    -   inhibitors of complex II: benodanil (A.3.1), benzovindiflupyr        (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5),        fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8),        fluxapyroxad (A.3.9), furametpyr (A.3.10), isofetamid (A.3.11),        isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.14),        penflufen (A.3.15), penthiopyrad (A.3.16), pydiflumetofen        (A.3.17), pyraziflumid (A.3.18), sedaxane (A.3.19), tecloftalam        (A.3.20), thifluzamide (A.3.21), inpyrfluxam (A.3.22),        pyrapropoyne (A.3.23), fluindapyr (A.3.28), methyl        (E)-2-[2-[(5-cyano-2-methyl-phenoxy)methyl]phenyl]-3-methoxy-prop-2-enoate        (A.3.30), isoflucypram (A.3.31),        2-(difluoromethyl)-N-(1,1,3-trimethyl-indan-4-yl)pyridine-3-carboxamide        (A.3.32),        2-(difluoromethyl)-N-[(3R)-1,1,3-trimethylindan-4-yl]pyridine-3-carboxamide        (A.3.33),        2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide        (A.3.34),        2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide        (A.3.35),        2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide        (A.3.36),        2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propyl-indan-4-yl]pyridine-3-carboxamide        (A.3.37),        2-(difluoromethyl)-N-(3-isobutyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide        (A.3.38),        2-(difluoromethyl)-N-[(3R)-3-isobutyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide        (A.3.39);    -   other respiration inhibitors: diflumetorim (A.4.1); nitrophenyl        derivates: binapacryl (A.4.2), dinobuton (A.4.3), dinocap        (A.4.4), fluazinam (A.4.5), meptyldinocap (A.4.6), ferimzone        (A.4.7); organometal compounds: fentin salts, e. g.        fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin        hydroxide (A.4.10); ametoctradin (A.4.11); silthiofam (A.4.12);

B) Sterol Biosynthesis Inhibitors (SBI Fungicides)

-   -   C14 demethylase inhibitors: triazoles: azaconazole (B.1.1),        bitertanol (B.1.2), bromu-conazole (B.1.3), cyproconazole        (B.1.4), difenoconazole (B.1.5), diniconazole (B.1.6),        diniconazole-M (B.1.7), epoxiconazole (B.1.8), fenbuconazole        (B.1.9), fluquinconazole (B.1.10), flusilazole (B.1.11),        flutriafol (B.1.12), hexaconazole (B.1.13), imibenconazole        (B.1.14), ipconazole (B.1.15), metconazole (B.1.17),        myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobutrazole        (B.1.20), penconazole (B.1.21), propiconazole (B.1.22),        prothio-conazole (B.1.23), simeconazole (B.1.24), tebuconazole        (B.1.25), tetraconazole (B.1.26), triadimefon (B.1.27),        triadimenol (B.1.28), triticonazole (B.1.29), uniconazole        (B.1.30),        2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridyl]propan-2-ol        (B.1.31),        2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]-2-pyridyl]propan-2-ol        (B.1.32), ipfentrifluconazole (B.1.37), mefentrifluconazole        (B.1.38),        2-(chloromethyl)-2-methyl-5-(p-tolylmethyl)-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol        (B.1.43); imidazoles: imazalil (B.1.44), pefurazoate (B.1.45),        prochloraz (B.1.46), triflumizol (B.1.47); pyrimidines,        pyridines, piperazines: fenarimol (B.1.49), pyrifenox (B.1.50),        triforine (B.1.51),        [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluoro-phenyl)isoxazol-4-yl]-(3-pyridyl)methanol        (B.1.52);    -   Delta14-reductase inhibitors: aldimorph (B.2.1), dodemorph        (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4),        tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7),        spiroxamine (B.2.8);    -   Inhibitors of 3-keto reductase: fenhexamid (B.3.1);    -   Other Sterol biosynthesis inhibitors: chlorphenomizole (B.4.1);

C) Nucleic Acid Synthesis Inhibitors

-   -   phenylamides or acyl amino acid fungicides: benalaxyl (C.1.1),        benalaxyl-M (C.1.2), kiralaxyl (C.1.3), metalaxyl (C.1.4),        metalaxyl-M (C.1.5), ofurace (C.1.6), oxadixyl (C.1.7);    -   other nucleic acid synthesis inhibitors: hymexazole (C.2.1),        octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4),        5-fluorocytosine (C.2.5),        5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine (C.2.6),        5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7),        5-fluoro-2-(4-chlorophenylmethoxy)pyrimidin-4 amine (C.2.8);

D) Inhibitors of Cell Division and Cytoskeleton

-   -   tubulin inhibitors: benomyl (D.1.1), carbendazim (D.1.2),        fuberidazole (D1.3), thiabendazole (D.1.4), thiophanate-methyl        (D.1.5), pyridachlometyl (D.1.6),        N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide        (D.1.8),        N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-acetamide        (D.1.9),        2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)butanamide        (D.1.10),        2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methoxy-acetamide        (D.1.11),        2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-propyl-butanamide        (D.1.12),        2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy-N-propyl-acetamide        (D.1.13),        2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-N-propyl-acetamide        (D.1.14),        2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methylsulfanyl-acetamide        (D.1.15),        4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine        (D.1.16);    -   other cell division inhibitors: diethofencarb (D.2.1), ethaboxam        (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide        (D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7);

E) Inhibitors of Amino Acid and Protein Synthesis

-   -   methionine synthesis inhibitors: cyprodinil (E.1.1), mepanipyrim        (E.1.2), pyrimethanil (E.1.3);    -   protein synthesis inhibitors: blasticidin-S (E.2.1), kasugamycin        (E.2.2), kasugamycin hydrochloride-hydrate (E.2.3), mildiomycin        (E.2.4), streptomycin (E.2.5), oxytetracyclin (E.2.6);

F) Signal Transduction Inhibitors

-   -   MAP/histidine kinase inhibitors: fluoroimid (F.1.1), iprodione        (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4), fludioxonil        (F.1.5);    -   G protein inhibitors: quinoxyfen (F.2.1);

G) Lipid and Membrane Synthesis Inhibitors

-   -   Phospholipid biosynthesis inhibitors: edifenphos (G.1.1),        iprobenfos (G.1.2), pyrazophos (G.1.3), isoprothiolane (G.1.4);    -   lipid peroxidation: dicloran (G.2.1), quintozene (G.2.2),        tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5),        chloroneb (G.2.6), etridiazole (G.2.7);    -   phospholipid biosynthesis and cell wall deposition: dimethomorph        (G.3.1), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph        (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6),        valifenalate (G.3.7);    -   compounds affecting cell membrane permeability and fatty acides:        propamocarb (G.4.1);    -   inhibitors of oxysterol binding protein: oxathiapiprolin        (G.5.1),        2-{3-[2-(1-{[3,5-bis(difluoromethyl-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-phenyl        methanesulfonate (G.5.2),        2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-acetyl}piperidin-4-yl)        1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl        methanesulfonate (G.5.3),        4-[1-[2-[3-(difluoromethyl)-5-methyl-pyrazol-1-yl]acetyl]-4-piperidy]-N-tetralin-1-yl-pyridine-2-carboxamide        (G.5.4),        4-[1-[2-[3,5-bis(difluoromethyl)pyrazo-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide        (G.5.5),        4-[1-[2-[3-(difluoromethyl)-5-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide        (G.5.6),        4-[1-[2-[5-cyclopropyl-3-(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide        (G.5.7),        4-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide        (G.5.8),        4-[1-[2-[5-(difluoromethyl)-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide        (G.5.9),        4-[1-[2-[3,5-bis(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide        (G.5.10),        (4-[1-[2-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide        (G.5.11);

H) Inhibitors with Multi Site Action

-   -   inorganic active substances: Bordeaux mixture (H.1.1), copper        (H.1.2), copper acetate (H.1.3), copper hydroxide (H.1.4),        copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur        (H.1.7);    -   thio- and dithiocarbamates: ferbam (H.2.1), mancozeb (H.2.2),        maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6),        thiram (H.2.7), zineb (H.2.8), ziram (H.2.9);    -   organochlorine compounds: anilazine (H.3.1), chlorothalonil        (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5),        dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene        (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide        (H.3.10), tolylfluanid (H.3.11);    -   guanidines and others: guanidine (H.4.1), dodine (H.4.2), dodine        free base (H.4.3), guazatine (H.4.4), guazatine-acetate (H.4.5),        iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7),        iminoctadine-tris(albesilate) (H.4.8), dithianon (H.4.9),        2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetraone        (H.4.10);

I) Cell Wall Synthesis Inhibitors

-   -   inhibitors of glucan synthesis: validamycin (I.1.1), polyoxin B        (I.1.2);    -   melanin synthesis inhibitors: pyroquilon (I.2.1), tricyclazole        (I.2.2), carpropamid (I.2.3), dicyclomet (I.2.4), fenoxanil        (I.2.5);

J) Plant Defence Inducers

-   -   acibenzolar-S-methyl (J.1.1), probenazole (J.1.2), isotianil        (J.1.3), tiadinil (J.1.4), prohexadione-calcium (J.1.5);        phosphonates: fosetyl (J.1.6), fosetyl-aluminum (J.1.7),        phosphorous acid and its salts (J.1.8), calcium phosphonate        (J.1.11), potassium phosphonate (J.1.12), potassium or sodium        bicarbonate (J.1.9),        4-cyclopropyl-N-(2,4-dimethoxyphenyl)thiadiazole-5-carboxamide        (J.1.10);

K) Unknown Mode of Action

-   -   bronopol (K.1.1), chinomethionat (K.1.2), cyflufenamid (K.1.3),        cymoxanil (K.1.4), dazomet (K.1.5), debacarb (K.1.6), diclocymet        (K.1.7), diclomezine (K.1.8), difenzoquat (K.1.9),        difenzoquat-methylsulfate (K.1.10), diphenylamin (K.1.11),        fenitropan (K.1.12), fenpyrazamine (K.1.13), flumetover        (K.1.14), flusulfamide (K.1.15), flutianil (K.1.16), harpin        (K.1.17), methasulfocarb (K.1.18), nitrapyrin (K.1.19),        nitrothal-isopropyl (K.1.20), tolprocarb (K.1.21), oxin-copper        (K.1.22), proquinazid (K.1.23), tebufloquin (K.1.24),        tecloftalam (K.1.25), triazoxide (K.1.26),        N′(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl        formamidine (K.1.27),        N′(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl        formamidine (K.1.28),        N′[4-[[3-[(4-chorophenyl)methyl]-1,2,4-thiadiazol-5-yl]-oxy]-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine        (K.1.29),        N′(5-bromo-6-indan-2-yloxy-2-methyl-3-pyridyl)-N-ethyl-N-methyl-formamidine        (K.1.30),        N′[5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine        (K.1.31),        N′[5-bromo-6-(4-isopropylcyclohexoxy)-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine        (K.1.32),        N′[5-bromo-2-methyl-6-(1-phenylethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine        (K.1.33),        N′(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl        formamidine (K.1.34),        N′(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl        formamidine (K.1.35),        2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide        (K.1.36),        3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine        (pyrisoxazole) (K.1.37),        3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3 yl]-pyridine        (K.1.38),        5-chloro-1-(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1H-benzoimidazole        (K.1.39), ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate        (K.1.40), picarbutrazox (K.1.41), pentyl        N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate        (K.1.42), but-3-ynyl        N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate        (K.1.43), ipflufenoquin (K.1.44), quinofumelin (K.1.47),        2-(6-benzyl-2-pyridyl)quinazoline (K.1.50),        2-[6-(3-fluoro-4-methoxy-phenyl)-5-methyl-2-pyridyl]quinazoline        (K.1.51), dichlobentiazox (K.1.52),        N′(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine        (K.1.53), pyrifenamine (K.1.54);

M) Growth Regulators

abscisic acid (M.1.1), amidochlor, ancymidol, 6-benzylaminopurine,brassinolide, butralin, chlormequat, chlormequat chloride, cholinechloride, cyclanilide, daminozide, dikegulac, dimethipin,2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet,forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid,maleic hydrazide, mefluidide, mepiquat, mepiquat chloride,naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione,prohexadione-calcium, prohydrojasmon, thidiazuron, triapenthenol,tributyl phosphorotrithioate, 2,3,5-tri-iodobenzoic acid,trinexapac-ethyl, uniconazole;

N) Herbicides from Classes N.1 to N.15

-   N.1 Lipid biosynthesis inhibitors: alloxydim, alloxydim-sodium,    butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim,    cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop,    fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop,    fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop,    haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop,    pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl,    quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl,    quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim,    4-(4′-chloro-4-cyclo¬propyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one    (1312337-72-6);    4-(2′,4′-dichloro-4-cyclopropyl[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one    (1312337-45-3);    4-(4′-chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one    (1033757-93-5);    4-(2′,4′-dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione    (1312340-84-3);    5-(acetyloxy)-4-(4′-chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one    (1312337-48-6);    5-(acetyloxy)-4-(2′,4′-dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one;    5-(acetyloxy)-4-(4′-chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one    (1312340-82-1);    5-(acetyloxy)-4-(2′,4′-di-chloro-4-ethyl[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one    (1033760-55-2);    4-(4′-chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethl-5-oxo-2H-pyran-3-yl    carbonic acid methyl ester (1312337-51-1);    4-(2′,4′-dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl    carbonic acid methyl ester;    4-(4′-chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl    carbonic acid methyl ester (1312340-83-2);    4-(2′,4′-dichloro-4-ethyl,[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl    carbonic acid methyl ester (1033760-58-5); benfuresate, butylate,    cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate,    flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA,    thiobencarb, tiocarbazil, triallate, vernolate;-   N.2 ALS inhibitors: amidosulfuron, azimsulfuron, bensulfuron,    bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron,    cinosulfuron, cyclosulfamuron, ethametsulfuron,    ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron,    flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium,    foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron,    iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron,    iofensulfuron-sodium, mesosulfuron, meta-zosulfuron, metsulfuron,    metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron,    primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron,    pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron,    sulfometuron-methyl, sulfosulfuron, thifensulfuron,    thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl,    trifloxysulfuron, triflusulfuron, triflusulfuron-methyl,    tritosulfuron, imazamethabenz, imazamethabenz-methyl, imazamox,    imazapic, imazapyr, imazaquin, imazethapyr; cloransulam,    cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam,    penoxsulam, pyrimisulfan, pyroxsulam; bispyribac, bispyribac-sodium,    pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl,    pyrithiobac, pyrithiobac-sodium,    4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic    acid-1-methylethyl ester (420138-41-6),    4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]-phenyl]¬methyl]amino]-benzoic    acid propyl ester (420138-40-5),    N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine    (420138-01-8); flucarbazone, flucarbazone-sodium, propoxycarbazone,    propoxycarbazone-sodium, thiencarbazone, thiencarbazone-methyl;    triafamone;-   N.3 Photosynthesis inhibitors: amicarbazone; chlorotriazine;    ametryn, atrazine, chloridazone, cyanazine, desmetryn,    dimethametryn, hexazinone, metribuzin, prometon, prometryn,    pro-pazine, simazine, simetryn, terbumeton, terbuthylazin,    terbutryn, trietazin; chlorobromuron, chlorotoluron, chloroxuron,    dimefuron, diuron, fluometuron, isoproturon, isouron, linuron,    metamitron, methabenzthiazuron, metobenzuron, metoxuron,    monolinuron, neburon, sidu-ron, tebuthiuron, thiadiazuron,    desmedipham, karbutilat, phenmedipham, phenmedipham-ethyl,    bromofenoxim, bromoxynil and its salts and esters, ioxynil and its    salts and esters, bromacil, lenacil, terbacil, bentazon,    bentazon-sodium, pyridate, pyridafol, pentanochlor, propanil;    diquat, diquat-dibromide, paraquat, paraquat-dichloride,    paraquat-dimetilsulfate;-   N.4 protoporphyrinogen-IX oxidase inhibitors: acifluorfen,    acifluorfen-sodium, azafenidin, ben-carbazone, benzfendizone,    bifenox, butafenacil, carfentrazone, carfentrazone-ethyl,    chlor-methoxyfen, cinidon-ethyl, fluazolate, flufenpyr,    flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin,    fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl,    fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen,    pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl,    saflufenacil, sulfentrazone, thidiazimin, tiafenacil,    trifludimoxazin, ethyl    [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimi-din-3-yl)phenoxy]-2-pyridyloxy]acetate    (353292-31-6),    N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide    (452098-92-9),    N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide    (915396-43-9),    N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethyl¬phenoxy)-5-methyl-1H-pyrazole-1-carboxamide    (452099-05-7),    N-tetrahydro¬furfuryl-3-(2-chloro-6-fluoro-4-trifluoro¬methylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide    (452100-03-7),    3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione    (451484-50-7),    2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione    (1300118-96-0),    1-methyl-6-trifluoro¬methyl-3-(2,2,7-tri-fluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione    (1304113-05-0), methyl    (E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1H-methyl-pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but-2-enoate    (948893-00-3),    3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione    (212754-02-4);-   N.5 Bleacher herbicides: beflubutamid, diflufenican, fluridone,    flurochloridone, flurtamone, norflurazon, picolinafen,    4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine    (180608-33-7); benzobicyclon, benzofenap, bicyclopyrone, clomazone,    fenquintrione, isoxaflutole, mesotrione, pyrasulfotole,    pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione,    tolpyralate, topramezone; aclonifen, amitrole, flumeturon;-   N.6 EPSP synthase inhibitors: glyphosate,    glyphosate-isopropylammonium, glyposate-potassium,    glyphosate-trimesium (sulfosate);-   N.7 Glutamine synthase inhibitors: bilanaphos (bialaphos),    bilanaphos-sodium, glufosinate, glufosinate-P, glufosinate-ammonium;-   N.8 DHP synthase inhibitors: asulam;-   N.9 Mitosis inhibitors: benfluralin, butralin, dinitramine,    ethalfluralin, fluchloralin, oryzalin, pen-dimethalin, prodiamine,    trifluralin; amiprophos, amiprophos-methyl, butamiphos; chlorthal,    chlorthal-dimethyl, dithiopyr, thiazopyr, propyzamide, tebutam;    carbetamide, chlorpropham, flamprop, flamprop-isopropyl,    flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, propham;-   N.10 VLCFA inhibitors: acetochlor, alachlor, butachlor,    dimethachlor, dimethenamid, dimethen-amid-P, metazachlor,    metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor,    prop-isochlor, thenylchlor, flufenacet, mefenacet, diphenamid,    naproanilide, napropamide, napro-pamide-M, fentrazamide, anilofos,    cafenstrole, fenoxasulfone, ipfencarbazone, piperophos,    pyroxasulfone, isoxazoline compounds of the formulae II.1, II.2,    II.3, II.4, II.5, II.6, II.7, II.8 and II.9

-   N.11 Cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil,    flupoxam, indaziflam, isoxaben, triaziflam,    1-cyclohexyl-5-pentafluorphenyloxy-14-[1,2,4,6]thiatriazin-3-ylamine    (175899-01-1);-   N.12 Decoupler herbicides: dinoseb, dinoterb, DNOC and its salts;-   N.13 Auxinic herbicides: 2,4-D and its salts and esters, clacyfos,    2,4-DB and its salts and esters, aminocyclopyrachlor and its salts    and esters, aminopyralid and its salts such as    aminopyralid-dimethylammonium,    aminopyralid-tris(2-hydroxypropyl)ammonium and its esters,    benazolin, benazolin-ethyl, chloramben and its salts and esters,    clomeprop, clopy-ralid and its salts and esters, dicamba and its    salts and esters, dichlorprop and its salts and esters,    dichlorprop-P and its salts and esters, fluroxypyr,    fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts    and esters (943832-60-8); MCPA and its salts and esters,    MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its    salts and esters, meco-prop-P and its salts and esters, picloram and    its salts and esters, quinclorac, quinmerac, TBA (2,3,6) and its    salts and esters, triclopyr and its salts and esters,    4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic    acid, benzyl    4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate    (1390661-72-9);-   N.14 Auxin transport inhibitors: diflufenzopyr,    diflufenzopyr-sodium, naptalam, naptalam-sodium;-   N.15 Other herbicides: bromobutide, chlorflurenol,    chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate    (499223-49-3) and its salts and esters, dalapon, dazomet,    difenzoquat, di-fenzoquat-metilsulfate, dimethipin, DSMA, dymron,    endothal and its salts, etobenzanid, flurenol, flurenol-butyl,    flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic    hydrazide, mefluidide, metam, methiozolin (403640-27-7), methyl    azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic    acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine,    tridiphane;

O) Insecticides from Classes 0.1 to 0.29

-   O.1 Acetylcholine esterase (AChE) inhibitors: aldicarb (O.1.1),    alanycarb (O.1.2), bendiocarb (O.1.3), benfuracarb (O.1.4),    butocarboxim (O.1.5), butoxycarboxim (O.1.6), carbaryl (O.1.7),    carbofuran (O.1.8), carbosulfan (O.1.9), ethiofencarb (O.1.10),    fenobucarb (O.1.11), formetanate (O.1.12), furathiocarb (O.1.13),    isoprocarb (O.1.14), methiocarb (O.1.15), methomyl (O.1.16),    metolcarb (O.1.17), oxamyl (O.1.18), pirimicarb (O.1.19), propoxur    (O.1.20), thiodicarb (O.1.21), thiofanox (O.1.22), trimethacarb    (O.1.23), XMC (O.1.24), xylylcarb (O.1.25), triazamate (O.1.26),    acephate (O.1.27), azamethiphos (O.1.28), azinphos-ethyl (O.1.29),    azinphosmethyl (O.1.30), cadusafos (O.1.31), chlorethoxyfos    (O.1.32), chlorfenvinphos (O.1.33), chlormephos (O.1.34),    chlorpyrifos (O.1.35), chlorpyrifos-methyl (O.1.36), coumaphos    (O.1.37), cyanophos (O.1.38), demeton-S-methyl (O.1.39), diazinon    (O.1.40), dichlorvos/DDVP (O.1.41), dicrotophos (O.1.42), dimethoate    (O.1.43), dimethylvinphos (O.1.44), disulfoton (O.1.45), EPN    (O.1.46), ethion (O.1.47), ethoprophos (O.1.48), famphur (O.1.49),    fenamiphos (O.1.50), fenitrothion (O.1.51), fenthion (O.1.52),    fosthiazate (O.1.53), heptenophos (O.1.54), imicyafos (O.1.55),    isofenphos (O.1.56), isopropyl 0-(methoxyaminothio-phosphoryl)    salicylate (O.1.57), isoxathion (O.1.58), malathion (O.1.59),    mecarbam (O.1.60), methamidophos (O.1.61), methidathion (O.1.62),    mevinphos (O.1.63), monocrotophos (O.1.64), naled (O.1.65),    omethoate (O.1.66), oxydemeton-methyl (O.1.67), parathion (O.1.68),    parathion-methyl (O.1.69), phenthoate (O.1.70), phorate (O.1.71),    phosalone (O.1.72), phosmet (O.1.73), phosphamidon (O.1.74), phoxim    (O.1.75), pirimiphos-methyl (O.1.76), profenofos (O.1.77),    propetamphos (O.1.78), prothiofos (O.1.79), pyraclofos (O.1.80),    pyridaphenthion (O.1.81), quinalphos (O.1.82), sulfotep (O.1.83),    tebupirimfos (O.1.84), temephos (O.1.85), terbufos (O.1.86),    tetrachlorvinphos (O.1.87), thiometon (O.1.88), triazophos (O.1.89),    trichlorfon (O.1.90), vamidothion (O.1.91);-   O.2 GABA-gated chloride channel antagonists: endosulfan (O.2.1),    chlordane (O.2.2), ethiprole (O.2.3), fipronil (O.2.4), flufiprole    (O.2.5), pyrafluprole (O.2.6), pyriprole (O.2.7);-   O.3 Sodium channel modulators: acrinathrin (O.3.1), allethrin    (O.3.2), d-cis-trans allethrin (O.3.3), d-trans allethrin (O.3.4),    bifenthrin (O.3.5), kappa-bifenthrin (O.3.6), bioallethrin (O.3.7),    bioallethrin S-cylclopentenyl (O.3.8), bioresmethrin (O.3.9),    cycloprothrin (O.3.10), cyfluthrin (O.3.11), beta-cyfluthrin    (O.3.12), cyhalothrin (O.3.13), lambda-cyhalothrin (O.3.14),    gamma-cyhalothrin (O.3.15), cypermethrin (O.3.16),    alpha-cypermethrin (O.3.17), beta-cypermethrin (O.3.18),    theta-cypermethrin (O.3.19), zeta-cypermethrin (O.3.20),    cyphenothrin (O.3.21), deltamethrin (O.3.22), empenthrin (O.3.23),    esfenvalerate (O.3.24), etofenprox (O.3.25), fenpropathrin (O.3.26),    fenvalerate (O.3.27), flucythrinate (O.3.28), flumethrin (O.3.29),    tau-fluvalinate (O.3.30), halfenprox (O.3.31), heptafluthrin    (O.3.32), imiprothrin (O.3.33), meperfluthrin (O.3.34), metofluthrin    (O.3.35), momfluorothrin (O.3.36), epsilon-momfluorothrin (O.3.37),    permethrin (O.3.38), phenothrin (O.3.39), prallethrin (O.3.40),    profluthrin (O.3.41), pyrethrin (pyrethrum) (O.3.42), resmethrin    (O.3.43), silafluofen (O.3.44), tefluthrin (O.3.45),    kappa-tefluthrin (O.3.46), tetramethylfluthrin (O.3.47),    tetramethrin (O.3.48), tralomethrin (O.3.49), transfluthrin    (O.3.50), DDT (O.3.51), methoxychlor (O.3.52);-   O.4 Nicotinic acetylcholine receptor agonists (nAChR): acetamiprid    (O.4.1), clothianidin (O.4.2), cycloxaprid (O.4.3), dinotefuran    (O.4.4), imidacloprid (O.4.5), nitenpyram (O.4.6), thiacloprid    (O.4.7), thiamethoxam (O.4.8),    4,5-dihydro-N-nitro-1-(2-oxiranylmethyl)-1H-imidazol-2-amine    (O.4.9),    (2E)-1-[(6-chloropyridin-3-yl)methyl]-N′-nitro-2-pentylidene-hydrazinecarboximidamide    (O.4.10),    1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine    (O.4.11), nicotine (O.4.12), sulfoxaflor (O.4.13), flupyradifurone    (O.4.14), triflumezopyrim (O.4.15);-   O.5 Nicotinic acetylcholine receptor allosteric activators: spinosad    (O.5.1), spinetoram (O.5.2);-   O.6 Chloride channel activators: abamectin (O.6.1), emamectin    benzoate (O.6.2), ivermectin (O.6.3), lepimectin (O.6.4),    milbemectin (O.6.5);-   O.7 Juvenile hormone mimics: hydroprene (O.7.1), kinoprene (O.7.2),    methoprene (O.7.3), fenoxycarb (O.7.4), pyriproxyfen (O.7.5);-   O.8 miscellaneous non-specific (multi-site) inhibitors: methyl    bromide (O.8.1) and other alkyl halides, chloropicrin (O.8.2),    sulfuryl fluoride (O.8.3), borax (O.8.4), tartar emetic (O.8.5);-   O.9 Chordotonal organ TRPV channel modulators: pymetrozine (O.9.1),    pyrifluquinazon (O.9.2), flonicamid (O.9.3);-   O.10 Mite growth inhibitors: clofentezine (O.10.1), hexythiazox    (O.10.2), diflovidazin (O.10.3), etoxazole (O.10.4);-   O.11 Microbial disruptors of insect midgut membranes: Bacillus    thuringiensis, Bacillus sphaericus and the insecticidal proteins    they produce: Bacillus thuringiensis subsp. lsraelensis (O.11.1),    Bacillus sphaericus (O.11.2), Bacillus thuringiensis subsp. aizawai    (O.11.3), Bacillus thuringiensis subsp. kurstaki (O.11.4), Bacillus    thuringiensis subsp. tenebrionis (O.11.5), the Bt crop proteins:    Cry1Ab (O.11.6), Cry1Ac (O.11.7), Cry1Fa (O.11.8), Cry2Ab (O.11.9),    mCry3A (O.11.10), Cry3Ab (O.11.11), Cry3Bb (O.11.12), Cry34/35Ab1    (O.11.13);-   O.12 Inhibitors of mitochondrial ATP synthase: diafenthiuron    (O.12.1), azocyclotin (O.12.2), cyhexatin (O.12.3), fenbutatin oxide    (O.12.4), propargite (O.12.5), tetradifon (O.12.6);-   O.13 Uncouplers of oxidative phosphorylation via disruption of the    proton gradient: chlorfenapyr (O.13.1), DNOC (O.13.2), sulfluramid    (O.13.3);-   O.14 Nicotinic acetylcholine receptor (nAChR) channel blockers:    bensultap (O.14.1), cartap hydrochloride (O.14.2), thiocyclam    (O.14.3), thiosultap sodium (O.14.4);-   O.15 Inhibitors of the chitin biosynthesis type 0: bistrifluron    (O.15.1), chlorfluazuron (O.15.2), diflubenzuron (O.15.3),    flucycloxuron (O.15.4), flufenoxuron (O.15.5), hexaflumuron    (O.15.6), lufenuron (O.15.7), novaluron (O.15.8), noviflumuron    (O.15.9), teflubenzuron (O.15.10), triflumuron (O.15.11);-   O.16 Inhibitors of the chitin biosynthesis type 1: buprofezin    (O.16.1);-   O.17 Moulting disruptors: cyromazine (O.17.1);-   O.18 Ecdyson receptor agonists: methoxyfenozide (O.18.1),    tebufenozide (O.18.2), halofenozide (O.18.3), fufenozide (O.18.4),    chromafenozide (O.18.5);-   O.19 Octopamin receptor agonists: amitraz (O.19.1);-   O.20 Mitochondrial complex III electron transport inhibitors:    hydramethylnon (O.20.1), acequinocyl (O.20.2), fluacrypyrim    (O.20.3), bifenazate (O.20.4);-   O.21 Mitochondrial complex I electron transport inhibitors:    fenazaquin (O.21.1), fenpyroximate (O.21.2), pyrimidifen (O.21.3),    pyridaben (O.21.4), tebufenpyrad (O.21.5), tolfenpyrad (O.21.6),    rotenone (O.21.7);-   O.22 Voltage-dependent sodium channel blockers: indoxacarb (O.22.1),    metaflumizonev (O.22.2),    2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide    (O.22.3),    N-(3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)-[4-[methyl(methylsulfonyl)amino]phenyl]methylene]-hydrazinecarboxamide    (O.22.4);-   O.23 Inhibitors of the of acetyl CoA carboxylase: spirodiclofen    (O.23.1), spiromesifen (O.23.2), spirotetramat (O.23.3), spiropidion    (O.23.4);-   O.24 Mitochondrial complex IV electron transport inhibitors:    aluminium phosphide (O.24.1), calcium phosphide (O.24.2), phosphine    (O.24.3), zinc phosphide (O.24.4), cyanide (O.24.5);-   O.25 Mitochondrial complex II electron transport inhibitors:    cyenopyrafen (O.25.1), cyflumetofen (O.25.2);-   O.26 Ryanodine receptor-modulators: flubendiamide (O.26.1),    chlorantraniliprole (O.26.2), cyantraniliprole (O.26.3),    cyclaniliprole (O.26.4), tetraniliprole (O.26.5),    (R)-3-chloro-N¹-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N²-(1-methyl-2-methylsulfonylethyl)phthalamide    (O.26.6),    (S)-3-chloro-N¹-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N²-(1-methyl-2-methylsulfonylethyl)phthalamide    (O.26.7),    methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}-amino)benzoyl]-1,2-dimethylhydrazinecarboxylate    (O.26.8),    N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide    (O.26.9),    N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide    (O.26.10),    N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide    (O.26.11),    N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide    (O.26.12),    N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide    (O.26.13),    N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide    (O.26.14),    3-chloro-1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1-cyano-1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide    (O.26.15),    3-bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-1-(3,5-dichloro-2-pyridyl)-1H-pyrazole-5-carboxamide    (O.26.16),    N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide    (O.26.17), cyhalodiamide (O.26.18);-   O.27: Chordotonal organ Modulators—undefined target site: flonicamid    (O.27.1);-   O.28. insecticidal active compounds of unknown or uncertain mode of    action: afidopyropen (O.28.1), afoxolaner (O.28.2), azadirachtin    (O.28.3), amidoflumet (O.28.4), benzoximate (O.28.5), broflanilide    (O.28.6), bromopropylate (O.28.7), chinomethionat (O.28.8), cryolite    (O.28.9), dicloromezotiaz (O.28.10), dicofol (O.28.11), flufenerim    (O.28.12), flometoquin (O.28.13), fluensulfone (O.28.14), fluhexafon    (O.28.15), fluopyram (O.28.16), fluralaner (O.28.17), metoxadiazone    (O.28.18), piperonyl butoxide (O.28.19), pyflubumide (O.28.20),    pyridalyl (O.28.21), tioxazafen (O.28.22),    11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-11-en-10-one,    3-(4′-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one,    1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine    (O.28.23), Bacillus firmus 1-1582 (O.28.24), flupyrimin (O.28.25),    fluazaindolizine (O.28.26),    4-[5-(3,5-di-chlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide    (O.28.27), fluxametamide (O.28.28),    5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole    (O.28.1),    4-cyano-N-[2-cyano-5-[[2,6-dibromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide    (O.28.29),    4-cyano-3-[(4-cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]-2-fluoro-benzamide    (O.28.30),    N-[5-[[2-chloro-6-cyano-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide    (O.28.31),    N-[5-[[2-bromo-6-chloro-4-[2,2,2-tri-fluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide    (O.28.32),    N-[5-[[2-bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide    (O.28.33),    4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]-carbamoyl]phenyl]-2-methyl-benzamide    (O.28.34),    4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide    (O.28.35),    N-[5-[[2-bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide    (O.28.36);    2-(1,3-dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine    (O.28.37),    2-[6-[2-(5-fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine    (O.28.38),    2-[6-[2-(3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine    (O.28.39),    N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide    (O.28.40),    N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide    (O.28.41),    1-[(6-chloro-3-pyridinyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1,2-a]pyridine    (O.28.42),    1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol    (O.28.43),    1-isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide    (O.28.44),    1-(1,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide    (O.28.45),    N,5-dimethyl-N-pyridazin-4-yl-1-(2,2,2-trifluoro-1-methyl-ethyl)pyrazole-4-carboxamide    (O.28.46),    1-[1-(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide    (O.28.47),    N-ethyl-1-(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide    (O.28.48),    1-(1,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide    (O.28.49),    1-[1-(1-cyanocyclopropyl)ethyl]-N,5-di-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide    (O.28.50),    N-methyl-1-(2-fluoro-1-methyl-propyl]-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide    (O.28.51),    1-(4,4-di-fluorocyclohexyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide    (O.28.52),    1-(4,4-difluorocyclohexyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide    (O.28.53),    N-(1-methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide    (O.28.54), N-cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide    (O.28.55), N-cyclohexyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide    (O.28.56),    2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4-carboxamide    (O.28.57),    2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole-5-carboxamide    (O.28.58), methyl    2-[[2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecarboxylate    (O.28.59),    N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide    (O.28.60),    N-(2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxamide    (O.28.61),    2-(3-pyridinyl)-N-(2-pyrimidinylmethyl)-2H-indazole-5-carboxamide    (O.28.62),    N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide    (O.28.63), tyclopyrazoflor (O.28.64), sarolaner (O.28.65), lotilaner    (O.28.66),    N-[4-chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1,1,2,2,2-penta-fluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide    (O.28.67), M.UN.22a    2-(3-ethylsulfonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine    (O.28.68),    2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine    (O.28.69),    4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide    (O.28.70),    4-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide    (O.28.71),    N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-2-methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide    (O.28.72),    N-[4-chloro-3-[(1-cy-anocyclopropyl)carbamoyl]phenyl]-2-methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)-pyrazole-3-carboxamide    (O.28.73), acynonapyr (O.28.74), benzpyrimoxan (O.28.75),    chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide    (O.28.76), oxazosulfyl (O.28.77),    [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl]-N-[4-[1-[4-(tri-fluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate    (O.28.78),    [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]    N-[4-[1-[4-(trifluoro-methoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate    (O.28.79),    [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl]-N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate    (O.28.80),    [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]-N-[4-[1-[4-(1,1,2,2,2-penta-fluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate    (O.28.81),    (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylenehydrazono]thiazolidin-4-one    (O.28.82).

The active substances referred to as component 2, their preparation andtheir activity e. g. against harmful fungi is known (cf.:http://www.alanwood.net/pesticides/); these substances are commerciallyavailable. The compounds described by IUPAC nomenclature, theirpreparation and their pesticidal activity are also known (cf. Can. J.Plant Sci. 48(6), 587-94, 1968; EP-A 141 317; EP-A 152 031; EP-A 226917; EP-A 243 970; EP-A 256 503; EP-A 428 941; EP-A 532 022; EP-A 1 028125; EP-A 1 035 122; EP-A 1 201 648; EP-A 1 122 244, JP 2002316902; DE19650197; DE 10021412; DE 102005009458; U.S. Pat. Nos. 3,296,272;3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO00/29404; WO 00/46148; WO 00/65913; WO 01/54501; WO 01/56358; WO02/22583; WO 02/40431; WO 03/10149; WO 03/11853; WO 03/14103; WO03/16286; WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491; WO04/49804; WO 04/83193; WO 05/120234; WO 05/123689; WO 05/123690; WO05/63721; WO 05/87772; WO 05/87773; WO 06/15866; WO 06/87325; WO06/87343; WO 07/82098; WO 07/90624, WO 10/139271, WO 11/028657, WO12/168188, WO 07/006670, WO 11/77514; WO 13/047749, WO 10/069882, WO13/047441, WO 03/16303, WO 09/90181, WO 13/007767, WO 13/010862, WO13/127704, WO 13/024009, WO 13/24010, WO 13/047441, WO 13/162072, WO13/092224, WO 11/135833, CN 1907024, CN 1456054, CN 103387541, CN1309897, WO 12/84812, CN 1907024, WO 09094442, WO 14/60177, WO13/116251, WO 08/013622, WO 15/65922, WO 94/01546, EP 2865265, WO07/129454, WO 12/165511, WO 11/081174, WO 13/47441). Some compounds areidentified by their CAS Registry Number which is separated by hyphensinto three parts, the first consisting from two up to seven digits, thesecond consisting of two digits, and the third consisting of a singledigit

The present invention furthermore relates to agrochemical compositionscomprising a mixture of at least one compound I (component 1) and atleast one further active substance useful for plant protection, e. g.selected from the groups A) to O) (component 2), in particular onefurther fungicide, e. g. one or more fungicide from the groups A) to K),as described above, and if desired one suitable solvent or solidcarrier. Those mixtures are of particular interest, since many of themat the same application rate show higher efficiencies against harmfulfungi. Furthermore, combating harmful fungi with a mixture of compoundsI and at least one fungicide from groups A) to K), as described above,is more efficient than combating those fungi with individual compounds Ior individual fungicides from groups A) to K).

By applying compounds I together with at least one active substance fromgroups A) to O) a synergistic effect can be obtained, i.e. more thensimple addition of the individual effects is obtained (synergisticmixtures).

This can be obtained by applying the compounds I and at least onefurther active substance simultaneously, either jointly (e. g. astank-mix) or separately, or in succession, wherein the time intervalbetween the individual applications is selected to ensure that theactive substance applied first still occurs at the site of action in asufficient amount at the time of application of the further activesubstance(s). The order of application is not essential for working ofthe present invention.

When applying compound I and a pesticide II sequentially the timebetween both applications may vary e. g. between 2 hours to 7 days. Alsoa broader range is possible ranging from 0.25 hour to 30 days,preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 daysor from 1.5 hours to 5 days, even more preferred from 2 hours to 1 day.

In the binary mixtures and compositions according to the invention theweight ratio of the component 1) and the component 2) generally dependsfrom the properties of the active components used, usually it is in therange of from 1:10,000 to 10,000:1, often it is in the range of from1:100 to 100:1, regularly in the range of from 1:50 to 50:1, preferablyin the range of from 1:20 to 20:1, more preferably in the range of from1:10 to 10:1, even more preferably in the range of from 1:4 to 4:1 andin particular in the range of from 1:2 to 2:1.

According to further embodiments of the binary mixtures andcompositions, the weight ratio of the component 1) and the component 2)usually is in the range of from 1000:1 to 1:1, often in the range offrom 100:1 to 1:1, regularly in the range of from 50:1 to 1:1,preferably in the range of from 20:1 to 1:1, more preferably in therange of from 10:1 to 1:1, even more preferably in the range of from 4:1to 1:1 and in particular in the range of from 2:1 to 1:1.

According to a further embodiments of the binary mixtures andcompositions, the weight ratio of the component 1) and the component 2)usually is in the range of from 1:1 to 1:1000, often in the range offrom 1:1 to 1:100, regularly in the range of from 1:1 to 1:50,preferably in the range of from 1:1 to 1:20, more preferably in therange of from 1:1 to 1:10, even more preferably in the range of from 1:1to 1:4 and in particular in the range of from 1:1 to 1:2.

In the ternary mixtures, i.e. compositions according to the inventioncomprising the component 1) and component 2) and a compound III(component 3), the weight ratio of component 1) and component 2) dependsfrom the properties of the active substances used, usually it is in therange of from 1:100 to 100:1, regularly in the range of from 1:50 to50:1, preferably in the range of from 1:20 to 20:1, more preferably inthe range of from 1:10 to 10:1 and in particular in the range of from1:4 to 4:1, and the weight ratio of component 1) and component 3)usually it is in the range of from 1:100 to 100:1, regularly in therange of from 1:50 to 50:1, preferably in the range of from 1:20 to20:1, more preferably in the range of from 1:10 to 10:1 and inparticular in the range of from 1:4 to 4:1.

Any further active components are, if desired, added in a ratio of from20:1 to 1:20 to the component 1).

These ratios are also suitable for inventive mixtures applied by seedtreatment.

Accordingly, the present invention furthermore relates to mixturescomprising one compound of the formula I (component 1, a grouprepresented by the expression “(1)”) and one pesticide II (component 2),wherein pesticide II is an active ingredients selected from the groupsA) to O) defined above.

Further embodiments B-1 to B-683 listed in Table B below relate tomixtures comprising as active components one of the in the presentspecification individualized compounds of the formula I, which isselected from the group of compounds I.A.A-1 to I.A.A-593, I.B.A-1 toI.B.A-593, I.C.A-1 to I.C.A-593, I.D.A-1 to I.D.A-593, I.E.A-1 toI.E.A-593, I.F.A-1 to I.F.A-593, I.G.A-1 to I.G.A-593, I.H.A-1 toI.H.A-593, I.J.A-1 to I.J.A-593 and I.K.A-1 to I.K.A-593 defined intables 1 to 10 (component 1, a group represented by the expression“(1)”) and one pesticide II selected from the groups A) to O) as definedherein (component 2, for example, (A.1.1) or azoxystrobin, in embodimentB-1).

Further embodiments B-1 to B-683 listed in Table B below relate to themixtures comprising as active components one of the in the presentspecification individualized compounds of the formula I, which isselected from the group of compounds Ex-1 to Ex-47 of formula I asdefined in Table I below (component 1, a group represented by theexpression “(1)”) and one pesticide II selected from the groups A) to O)as defined herein (component 2, for example, (A.1.1) or azoxystrobin, inembodiment B-1).

Preferably, the compositions described in Table B comprise the activecomponents in synergistically effective amounts.

Table B:

B-1: (I)+(A.1.1), B-2: (I)+(A.1.2), B-3: (I)+(A.1.3), B-4: (I)+(A.1.4),B-5: (I)+(A.1.5), B-6: (I)+(A.1.6), B-7: (I)+(A.1.7), B-8: (I)+(A.1.8),B-9: (I)+(A.1.9), B-10: (I)+(A.1.10), B-11: (I)+(A.1.11), B-12:(I)+(A.1.12), B-13: (I)+(A.1.13), B-14: (I)+(A.1.14), B-15:(I)+(A.1.15), B-16: (I)+(A.1.16), B-17: (I)+(A.1.17), B-18:(I)+(A.1.18), B-19: (I)+(A.1.19), B-20: (I)+(A.1.20), B-21:(I)+(A.1.21), B-22: (I)+(A.1.21a), B-23: (I)+(A.1.22), B-24:(I)+(A.1.25), B-25: (I)+(A.1.34), B-26: (I)+(A.1.35), B-27:(I)+(A.1.36), B-28: (I)+(A.1.37), B-29: (I)+(A.1.38), B-30: (I)+(A.2.1),B-31: (I)+(A.2.2), B-32: (I)+(A.2.3), B-33: (I)+(A.2.4), B-34:(I)+(A.2.5), B-35: (I)+(A.3.1), B-36: (I)+(A.3.2), B-37: (I)+(A.3.3),B-38: (I)+(A.3.4), B-39: (I)+(A.3.5), B-40: (I)+(A.3.6), B-41:(I)+(A.3.7), B-42: (I)+(A.3.8), B-43: (I)+(A.3.9), B-44: (I)+(A.3.10),B-45: (I)+(A.3.11), B-46: (I)+(A.3.12), B-47: (I)+(A.3.13), B-48:(I)+(A.3.14), B-49: (I)+(A.3.15), B-50: (I)+(A.3.16), B-51:(I)+(A.3.17), B-52: (I)+(A.3.18), B-53: (I)+(A.3.19), B-54:(I)+(A.3.20), B-55: (I)+(A.3.21), B-56: (I)+(A.3.22), B-57:(I)+(A.3.23), B-58: (I)+(A.3.24), B-59: (I)+(A.3.25), B-60:(I)+(A.3.26), B-61: (I)+(A.3.27), B-62: (I)+(A.3.28), B-63:(I)+(A.3.30), B-64: (I)+(A.3.31), B-65: (I)+(A.3.32), B-66:(I)+(A.3.33), B-67: (I)+(A.3.34), B-68: (I)+(A.3.35), B-69:(I)+(A.3.36), B-70: (I)+(A.3.37), B-71: (I)+(A.3.38), B-72:(I)+(A.3.39), B-73: (I)+(A.4.1), B-74: (I)+(A.4.2), B-75: (I)+(A.4.3),B-76: (I)+(A.4.4), B-77: (I)+(A.4.5), B-78: (I)+(A.4.6), B-79:(I)+(A.4.7), B-80: (I)+(A.4.8), B-81: (I)+(A.4.9), B-82: (I)+(A.4.10),B-83: (I)+(A.4.11), B-84: (I)+(A.4.12), B-85: (I)+(B.1.1), B-86:(I)+(B.1.2), B-87: (I)+(B.1.3), B-88: (I)+(B.1.4), B-89: (I)+(B.1.5),B-90: (I)+(B.1.6), B-91: (I)+(B.1.7), B-92: (I)+(B.1.8), B-93:(I)+(B.1.9), B-94: (I)+(B.1.10), B-95: (I)+(B.1.11), B-96: (I)+(B.1.12),B-97: (I)+(B.1.13), B-98: (I)+(B.1.14), B-99: (I)+(B.1.15), B-100:(I)+(B.1.16), B-101: (I)+(B.1.17), B-102: (I)+(B.1.18), B-103:(I)+(B.1.19), B-104: (I)+(B.1.20), B-105: (I)+(B.1.21), B-106:(I)+(B.1.22), B-107: (I)+(B.1.23), B-108: (I)+(B.1.24), B-109:(I)+(B.1.25), B-110: (I)+(B.1.26), B-111: (I)+(B.1.27), B-112:(I)+(B.1.28), B-113: (I)+(B.1.29), B-114: (I)+(B.1.30), B-115:(I)+(B.1.31), B-116: (I)+(B.1.32), B-117: (I)+(B.1.37), B-118:(I)+(B.1.38), B-119: (I)+(B.1.39), B-120: (I)+(B.1.40), B-121:(I)+(B.1.41), B-122: (I)+(B.1.42), B-123: (I)+(B.1.43), B-124:(I)+(B.1.44), B-125: (I)+(B.1.45), B-126: (I)+(B.1.46), B-127:(I)+(B.1.47), B-128: (I)+(B.1.48), B-129: (I)+(B.1.49), B-130:(I)+(B.1.50), B-131: (I)+(B.1.51), B-132: (I)+(B.1.52), B-133:(I)+(B.2.1), B-134: (I)+(B.2.2), B-135: (I)+(B.2.3), B-136: (I)+(B.2.4),B-137: (I)+(B.2.5), B-138: (I)+(B.2.6), B-139: (I)+(B.2.7), B-140:(I)+(B.2.8), B-141: (I)+(B.3.1), B-142: (I)+(B.4.1), B-143: (I)+(C.1.1),B-144: (I)+(C.1.2), B-145: (I)+(C.1.3), B-146: (I)+(C.1.4), B-147:(I)+(C.1.5), B-148: (I)+(C.1.6), B-149: (I)+(C.1.7), B-150: (I)+(C.2.1),B-151: (I)+(C.2.2), B-152: (I)+(C.2.3), B-153: (I)+(C.2.4), B-154:(I)+(C.2.5), B-155: (I)+(C.2.6), B-156: (I)+(C.2.7), B-157: (I)+(C.2.8),B-158: (I)+(D.1.1), B-159: (I)+(D.1.2), B-160: (I)+(D.1.3), B-161:(I)+(D.1.4), B-162: (I)+(D.1.5), B-163: (I)+(D.1.6), B-164: (I)+(D.1.7),B-165: (I)+(D.1.8), B-166: (I)+(D.1.9), B-167: (I)+(D.1.10), B-168:(I)+(D.1.11), B-169: (I)+(D.1.12), B-170: (I)+(D.1.13), B-171:(I)+(D.1.14), B-172: (I)+(D.1.15), B-173: (I)+(D.1.16), B-174:(I)+(D.2.1), B-175: (I)+(D.2.2), B-176: (I)+(D.2.3), B-177: (I)+(D.2.4),B-178: (I)+(D.2.5), B-179: (I)+(D.2.6), B-180: (I)+(D.2.7), B-181:(I)+(E.1.1), B-182: (I)+(E.1.2), B-183: (I)+(E.1.3), B-184: (I)+(E.2.1),B-185: (I)+(E.2.2), B-186: (I)+(E.2.3), B-187: (I)+(E.2.4), B-188:(I)+(E.2.5), B-189: (I)+(E.2.6), B-190: (I)+(F.1.1), B-191: (I)+(F.1.2),B-192: (I)+(F.1.3), B-193: (I)+(F.1.4), B-194: (I)+(F.1.5), B-195:(I)+(F.2.1), B-196: (I)+(G.1.1), B-197: (I)+(G.1.2), B-198: (I)+(G.1.3),B-199: (I)+(G.1.4), B-200: (I)+(G.2.1), B-201: (I)+(G.2.2), B-202:(I)+(G.2.3), B-203: (I)+(G.2.4), B-204: (I)+(G.2.5), B-205: (I)+(G.2.6),B-206: (I)+(G.2.7), B-207: (I)+(G.3.1), B-208: (I)+(G.3.2), B-209:(I)+(G.3.3), B-210: (I)+(G.3.4), B-211: (I)+(G.3.5), B-212: (I)+(G.3.6),B-213: (I)+(G.3.7), B-214: (I)+(G.4.1), B-215: (I)+(G.5.1), B-216:(I)+(G.5.2), B-217: (I)+(G.5.3), B-218: (I)+(G.5.4), B-219: (I)+(G.5.5),B-220: (I)+(G.5.6), B-221: (I)+(G.5.7), B-222: (I)+(G.5.8), B-223:(I)+(G.5.9), B-224: (I)+(G.5.10), B-225: (I)+(G.5.11), B-226:(I)+(H.1.1), B-227: (I)+(H.1.2), B-228: (I)+(H.1.3), B-229: (I)+(H.1.4),B-230: (I)+(H.1.5), B-231: (I)+(H.1.6), B-232: (I)+(H.1.7), B-233:(I)+(H.2.1), B-234: (I)+(H.2.2), B-235: (I)+(H.2.3), B-236: (I)+(H.2.4),B-237: (I)+(H.2.5), B-238: (I)+(H.2.6), B-239: (I)+(H.2.7), B-240:(I)+(H.2.8), B-241: (I)+(H.2.9), B-242: (I)+(H.3.1), B-243: (I)+(H.3.2),B-244: (I)+(H.3.3), B-245: (I)+(H.3.4), B-246: (I)+(H.3.5), B-247:(I)+(H.3.6), B-248: (I)+(H.3.7), B-249: (I)+(H.3.8), B-250: (I)+(H.3.9),B-251: (I)+(H.3.10), B-252: (I)+(H.3.11), B-253: (I)+(H.4.1), B-254:(I)+(H.4.2), B-255: (I)+(H.4.3), B-256: (I)+(H.4.4), B-257: (I)+(H.4.5),B-258: (I)+(H.4.6), B-259: (I)+(H.4.7), B-260: (I)+(H.4.8), B-261:(I)+(H.4.9), B-262: (I)+(H.4.10), B-263: (I)+(I.1.1), B-264:(I)+(I.1.2), B-265: (I)+(I.2.1), B-266: (I)+(I.2.2), B-267: (I)+(I.2.3),B-268: (I)+(I.2.4), B-269: (I)+(I.2.5), B-270: (I)+(J.1.1), B-271:(I)+(J.1.2), B-272: (I)+(J.1.3), B-273: (I)+(J.1.4), B-274: (I)+(J.1.5),B-275: (I)+(J.1.6), B-276: (I)+(J.1.7), B-277: (I)+(J.1.8), B-278:(I)+(J.1.9), B-279: (I)+(J.1.10), B-280: (I)+(K.1.1), B-281:(I)+(K.1.2), B-282: (I)+(K.1.3), B-283: (I)+(K.1.4), B-284: (I)+(K.1.5),B-285: (I)+(K.1.6), B-286: (I)+(K.1.7), B-287: (I)+(K.1.8), B-288:(I)+(K.1.9), B-289: (I)+(K.1.10), B-290: (I)+(K.1.11), B-291:(I)+(K.1.12), B-292: (I)+(K.1.13), B-293: (I)+(K.1.14), B-294:(I)+(K.1.15), B-295: (I)+(K.1.16), B-296: (I)+(K.1.17), B-297:(I)+(K.1.18), B-298: (I)+(K.1.19), B-299: (I)+(K.1.20), B-300:(I)+(K.1.21), B-301: (I)+(K.1.22), B-302: (I)+(K.1.23), B-303:(I)+(K.1.24), B-304: (I)+(K.1.25), B-305: (I)+(K.1.26), B-306:(I)+(K.1.27), B-307: (I)+(K.1.28), B-308: (I)+(K.1.29), B-309:(I)+(K.1.30), B-310: (I)+(K.1.31), B-311: (I)+(K.1.32), B-312:(I)+(K.1.33), B-313: (I)+(K.1.34), B-314: (I)+(K.1.35), B-315:(I)+(K.1.36), B-316: (I)+(K.1.37), B-317: (I)+(K.1.38), B-318:(I)+(K.1.39), B-319: (I)+(K.1.40), B-320: (I)+(K.1.41), B-321:(I)+(K.1.42), B-322: (I)+(K.1.43), B-323: (I)+(K.1.44), B-324:(I)+(K.1.45), B-325: (I)+(K.1.46), B-326: (I)+(K.1.47), B-327:(I)+(K.1.48), B-328: (I)+(K.1.49), B-329: (I)+(K.1.50), B-330:(I)+(K.1.51), B-331: (I)+(K.1.52), B-332: (I)+(K.1.53), B-333:(I)+(K.1.54), B-334: (I)+(O.1.1), B-335: (I)+(O.1.2), B-336:(I)+(O.1.3), B-337: (I)+(O.1.4), B-338: (I)+(O.1.5), B-339: (I)+(O.1.6),B-340: (I)+(O.1.7), B-341: (I)+(O.1.8), B-342: (I)+(O.1.9), B-343:(I)+(O.1.10), B-344: (I)+(O.1.11), B-345: (I)+(O.1.12), B-346:(I)+(O.1.13), B-347: (I)+(O.1.14), B-348: (I)+(O.1.15), B-349:(I)+(O.1.16), B-350: (I)+(O.1.17), B-351: (I)+(O.1.18), B-352:(I)+(O.1.19), B-353: (I)+(O.1.20), B-354: (I)+(O.1.21), B-355:(I)+(O.1.22), B-356: (I)+(O.1.23), B-357: (I)+(O.1.24), B-358:(I)+(O.1.25), B-359: (I)+(O.1.26), B-360: (I)+(O.1.27), B-361:(I)+(O.1.28), B-362: (I)+(O.1.29), B-363: (I)+(O.1.30), B-364:(I)+(O.1.31), B-365: (I)+(O.1.32), B-366: (I)+(O.1.33), B-367:(I)+(O.1.34), B-368: (I)+(O.1.35), B-369: (I)+(O.1.36), B-370:(I)+(O.1.37), B-371: (I)+(O.1.38), B-372: (I)+(O.1.39), B-373:(I)+(O.1.40), B-374: (I)+(O.1.41), B-375: (I)+(O.1.42), B-376:(I)+(O.1.43), B-377: (I)+(O.1.44), B-378: (I)+(O.1.45), B-379:(I)+(O.1.46), B-380: (I)+(O.1.47), B-381: (I)+(O.1.48), B-382:(I)+(O.1.49), B-383: (I)+(O.1.50), B-384: (I)+(O.1.51), B-385:(I)+(O.1.52), B-386: (I)+(O.1.53), B-387: (I)+(O.1.54), B-388:(I)+(O.1.55), B-389: (I)+(O.1.56), B-390: (I)+(O.1.57), B-391:(I)+(O.1.58), B-392: (I)+(O.1.59), B-393: (I)+(O.1.60), B-394:(I)+(O.1.61), B-395: (I)+(O.1.62), B-396: (I)+(O.1.63), B-397:(I)+(O.1.64), B-398: (I)+(O.1.65), B-399: (I)+(O.1.66), B-400:(I)+(O.1.67), B-401: (I)+(O.1.68), B-402: (I)+(O.1.69), B-403:(I)+(O.1.70), B-404: (I)+(O.1.71), B-405: (I)+(O.1.72), B-406:(I)+(O.1.73), B-407: (I)+(O.1.74), B-408: (I)+(O.1.75), B-409:(I)+(O.1.76), B-410: (I)+(O.1.77), B-411: (I)+(O.1.78), B-412:(I)+(O.1.79), B-413: (I)+(O.1.80), B-414: (I)+(O.1.81), B-415:(I)+(O.1.82), B-416: (I)+(O.1.83), B-417: (I)+(O.1.84), B-418:(I)+(O.1.85), B-419: (I)+(O.1.86), B-420: (I)+(O.1.87), B-421:(I)+(O.1.88), B-422: (I)+(O.1.89), B-423: (I)+(O.1.90), B-424:(I)+(O.1.91), B-425: (I)+(O.2.1), B-426: (I)+(O.2.2), B-427:(I)+(O.2.3), B-428: (I)+(O.2.4), B-429: (I)+(O.2.5), B-430: (I)+(O.2.6),B-431: (I)+(O.2.7), B-432: (I)+(O.3.1), B-433: (I)+(O.3.2), B-434:(I)+(O.3.3), B-435: (I)+(O.3.4), B-436: (I)+(O.3.5), B-437: (I)+(O.3.6),B-438: (I)+(O.3.7), B-439: (I)+(O.3.8), B-440: (I)+(O.3.9), B-441:(I)+(O.3.10), B-442: (I)+(O.3.11), B-443: (I)+(O.3.12), B-444:(I)+(O.3.13), B-445: (I)+(O.3.14), B-446: (I)+(O.3.15), B-447:(I)+(O.3.16), B-448: (I)+(O.3.17), B-449: (I)+(O.3.18), B-450:(I)+(O.3.19), B-451: (I)+(O.3.20), B-452: (I)+(O.3.21), B-453:(I)+(O.3.22), B-454: (I)+(O.3.23), B-455: (I)+(O.3.24), B-456:(I)+(O.3.25), B-457: (I)+(O.3.26), B-458: (I)+(O.3.27), B-459:(I)+(O.3.28), B-460: (I)+(O.3.29), B-461: (I)+(O.3.30), B-462:(I)+(O.3.31), B-463: (I)+(O.3.32), B-464: (I)+(O.3.33), B-465:(I)+(O.3.34), B-466: (I)+(O.3.35), B-467: (I)+(O.3.36), B-468:(I)+(O.3.37), B-469: (I)+(O.3.38), B-470: (I)+(O.3.39), B-471:(I)+(O.3.40), B-472: (I)+(O.3.41), B-473: (I)+(O.3.42), B-474:(I)+(O.3.43), B-475: (I)+(O.3.44), B-476: (I)+(O.3.45), B-477:(I)+(O.3.46), B-478: (I)+(O.3.47), B-479: (I)+(O.3.48), B-480:(I)+(O.3.49), B-481: (I)+(O.3.50), B-482: (I)+(O.3.51), B-483:(I)+(O.3.52), B-484: (I)+(O.4.1), B-485: (I)+(O.4.2), B-486:(I)+(O.4.3), B-487: (I)+(O.4.4), B-488: (I)+(O.4.5), B-489: (I)+(O.4.6),B-490: (I)+(O.4.7), B-491: (I)+(O.4.8), B-492: (I)+(O.4.9), B-493:(I)+(O.4.10), B-494: (I)+(O.4.11), B-495: (I)+(O.4.12), B-496:(I)+(O.4.13), B-497: (I)+(O.4.14), B-498: (I)+(O.4.15), B-499:(I)+(O.5.1), B-500: (I)+(O.5.2), B-501: (I)+(O.6.1), B-502: (I)+(O.6.2),B-503: (I)+(O.6.3), B-504: (I)+(O.6.4), B-505: (I)+(O.6.5), B-506:(I)+(O.7.1), B-507: (I)+(O.7.2), B-508: (I)+(O.7.3), B-509: (I)+(O.7.4),B-510: (I)+(O.7.5), B-511: (I)+(O.8.1), B-512: (I)+(O.8.2), B-513:(I)+(O.8.3), B-514: (I)+(O.8.4), B-515: (I)+(O.8.5), B-516: (I)+(O.9.1),B-517: (I)+(O.9.2), B-518: (I)+(O.9.3), B-519: (I)+(O.10.1), B-520:(I)+(O.10.2), B-521: (I)+(O.10.3), B-522: (I)+(O.10.4), B-523:(I)+(O.11.1), B-524: (I)+(O.11.2), B-525: (I)+(O.11.3), B-526:(I)+(O.11.4), B-527: (I)+(O.11.5), B-528: (I)+(O.11.6), B-529:(I)+(O.11.7), B-530: (I)+(O.11.8), B-531: (I)+(O.11.9), B-532:(I)+(O.11.10), B-533: (I)+(O.11.11), B-534: (I)+(O.11.12), B-535:(I)+(O.11.13), B-536: (I)+(O.12.1), B-537: (I)+(O.12.2), B-538:(I)+(O.12.3), B-539: (I)+(O.12.4), B-540: (I)+(O.12.5), B-541:(I)+(O.12.6), B-542: (I)+(O.13.1), B-543: (I)+(O.13.2), B-544:(I)+(O.13.3), B-545: (I)+(O.14.1), B-546: (I)+(O.14.2), B-547:(I)+(O.14.3), B-548: (I)+(O.14.4), B-549: (I)+(O.15.1), B-550:(I)+(O.15.2), B-551: (I)+(O.15.3), B-552: (I)+(O.15.4), B-553:(I)+(O.15.5), B-554: (I)+(O.15.6), B-555: (I)+(O.15.7), B-556:(I)+(O.15.8), B-557: (I)+(O.15.9), B-558: (I)+(O.15.10), B-559:(I)+(O.15.11), B-560: (I)+(O.16.1), B-561: (I)+(O.17.1), B-562:(I)+(O.18.1), B-563: (I)+(O.18.2), B-564: (I)+(O.18.3), B-565:(I)+(O.18.4), B-566: (I)+(O.18.5), B-567: (I)+(O.19.1), B-568:(I)+(O.20.1), B-569: (I)+(O.20.2), B-570: (I)+(O.20.3), B-571:(I)+(O.20.4), B-572: (I)+(O.21.1), B-573: (I)+(O.21.2), B-574:(I)+(O.21.3), B-575: (I)+(O.21.4), B-576: (I)+(O.21.5), B-577:(I)+(O.21.6), B-578: (I)+(O.21.7), B-579: (I)+(O.22.1), B-580:(I)+(O.22.2), B-581: (I)+(O.22.3), B-582: (I)+(O.22.4), B-583:(I)+(O.23.1), B-584: (I)+(O.23.2), B-585: (I)+(O.23.3), B-586:(I)+(O.23.4), B-587: (I)+(O.24.1), B-588: (I)+(O.24.2), B-589:(I)+(O.24.3), B-590: (I)+(O.24.4), B-591: (I)+(O.24.5), B-592:(I)+(O.25.1), B-593: (I)+(O.25.2), B-594: (I)+(O.26.1), B-595:(I)+(O.26.2), B-596: (I)+(O.26.3), B-597: (I)+(O.26.4), B-598:(I)+(O.26.5), B-599: (I)+(O.26.6), B-600: (I)+(O.26.7), B-601:(I)+(O.26.8), B-602: (I)+(O.26.9), B-603: (I)+(O.26.10), B-604:(I)+(O.26.11), B-605: (I)+(O.26.12), B-606: (I)+(O.26.13), B-607:(I)+(O.26.14), B-608: (I)+(O.26.15), B-609: (I)+(O.26.16), B-610:(I)+(O.26.17), B-611: (I)+(O.26.18), B-612: (I)+(O.27.1), B-613:(I)+(O.28.1), B-614: (I)+(O.28.2), B-615: (I)+(O.28.3), B-616:(I)+(O.28.4), B-617: (I)+(O.28.5), B-618: (I)+(O.28.7), B-619:(I)+(O.28.8), B-620: (I)+(O.28.9), B-621: (I)+(O.28.10), B-622:(I)+(O.28.11), B-623: (I)+(O.28.12), B-624: (I)+(O.28.13), B-625:(I)+(O.28.14), B-626: (I)+(O.28.15), B-627: (I)+(O.28.16), B-628:(I)+(O.28.17), B-629: (I)+(O.28.18), B-630: (I)+(O.28.19), B-631:(I)+(O.28.20), B-632: (I)+(O.28.21), B-633: (I)+(O.28.22), B-634:(I)+(O.28.23), B-635: (I)+(O.28.24), B-636: (I)+(O.28.25), B-637:(I)+(O.28.26), B-638: (I)+(O.28.27), B-639: (I)+(O.28.28), B-640:(I)+(O.28.29), B-641: (I)+(O.28.30), B-642: (I)+(O.28.31), B-643:(I)+(O.28.42), B-644: (I)+(O.28.43), B-645: (I)+(O.28.44), B-646:(I)+(O.28.45), B-647: (I)+(O.28.46), B-648: (I)+(O.28.47), B-649:(I)+(O.28.48), B-650: (I)+(O.28.49), B-651: (I)+(O.28.50), B-652:(I)+(O.28.51), B-653: (I)+(O.28.52), B-654: (I)+(O.28.53), B-655:(I)+(O.28.54), B-656: (I)+(O.28.55), B-657: (I)+(O.28.56), B-658:(I)+(O.28.57), B-659: (I)+(O.28.58), B-660: (I)+(O.28.59), B-661:(I)+(O.28.60), B-662: (I)+(O.28.61), B-663: (I)+(O.28.62), B-664:(I)+(O.28.63), B-665: (I)+(O.28.64), B-666: (I)+(O.28.65), B-667:(I)+(O.28.66), B-668: (I)+(O.28.67), B-669: (I)+(O.28.68), B-670:(I)+(O.28.69), B-671: (I)+(O.28.70), B-672: (I)+(O.28.71), B-673:(I)+(O.28.72), B-674: (I)+(O.28.73), B-675: (I)+(O.28.74), B-676:(I)+(O.28.75), B-677: (I)+(O.28.76), B-678: (I)+(O.28.77), B-679:(I)+(O.28.78), B-680: (I)+(O.28.79), B-681: (I)+(O.28.80), B-682:(I)+(O.28.81), B-683: (I)+(O.28.82).

The mixtures of active substances can be prepared as compositionscomprising besides the active ingredients at least one inert ingredient(auxiliary) by usual means, e. g. by the means given for thecompositions of compounds I.

Concerning usual ingredients of such compositions reference is made tothe explanations given for the compositions containing compounds I.

The mixtures of active substances according to the present invention aresuitable as fungicides, as are the compounds of formula I. They aredistinguished by an outstanding effectiveness against a broad spectrumof phytopathogenic fungi, especially from the classes of theAscomycetes, Basidiomycetes, Deuteromycetes and Peronosporomycetes (syn.Oomycetes). In addition, it is referred to the explanations regardingthe fungicidal activity of the compounds and the compositions containingcompounds I, respectively.

I. SYNTHESIS EXAMPLES

The compounds of the formula I can be prepared according to the methodsoutlined below.

I.1) Preparation of 4-(methylaminomethyl)benzonitrile

To a solution of 4-(bromomethyl)benzonitrile (49 g, 1 eq.) intetrahydrofurane (500 mL) methylamine (194 g of a 40% solution byweight, 10 eq.) was added. The mixture was stirred overnight at roomtemperature. After removing the solvent under reduced pressure, anaqueous solution of sodium chloride was added and the aqueous mixturewas extracted with ethyl acetate. The combined organic layer was driedwith magnesium sulfate and freed from solvent.

The title compound (35.6 g) was used directly without furtherpurification.

I.2) Preparation of N-[(4-cyanophenyl)methyl]-N-methyl-propanamide

To a solution of 4-(methylaminomethyl)benzonitrile (4.5 g, 1 eq.) intetrahydrufurane (50 mL) propionyl chloride (3.1 g, 1.1 eq.) was added.After stirring for one minute ethyl diisopropyl-amide (6 g, 1.5 eq.) wasadded and the mixture was stirred an additional one hour at roomtemperature. The title compound was used directly without furtherpurification.

I.3) Preparation ofN-[[4-[(Z)—N′-hydroxycarbamimidoyl]phenyl]methyl]-N-methyl propanamide

A solution of N-[(4-cyanophenyl)methyl]-N-methyl-propanamide (6.2 g, 1eq.), hydroxylamine hydrochloride (3.2 g, 1.5 eq.), potassium carbonate(2.8 g, 0.7 eq.), water (15 mL) and ethanol (30 mL) was stirredovernight at room temperature. The organic solvent was removed underreduced pressure, 40 mL toluol was added, stirred and removed again. Thetitle compound was used directly without further purification.

I.4) Preparation ofN-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide

To a solution ofN-[[4-[(Z)—N′-hydroxycarbamimidoyl]phenyl]methyl]-N-methyl-propanamide(7.2 g, 1 eq.) in tetrahydrofurane (100 mL) and N,N-dimethylformamide(20 mL) gradually trifluoroacetic anhydride (12 mL) was added. Themixture was stirred at 50° C. until HPLC indicated complete conversionof the starting material. In case the conversion was not complete moretrifluoroacetic anhydride was added. The solvent was removed underreduced pressure, water was added and the aqueous layer was extractedwith etylacetate. The organic layer was poured into dichloromethane andwashed with an aqueous solution of hydrochloric acid (1N solution)followed by an aqueous solution of sodium hydrogen carbonate. Theorganic layer was dried with magnesium sulfate and the solvent wasremoved under reduced pressure. The crude product was purified by columnchromatography (cyclohexane: ethyl acetate) to afford the desiredproduct as a colorless solid (5 g, 52%). Melting point: 30° C., LC/MS:Retention time (R_(t)) 1.146 min, ¹H NMR (400 MHz, CDCl₃): δ [ppm]=8.1(2H), 7.4 (2H), 4.7 (2H), 3.0 (3H), 2.5 (2H), 1.2 (3H).

I.5) Preparation ofN-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanethioamide(Ex-7, Example not According to the Invention)

To a solution ofN-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-propanamide(0.20 g, 1 eq.) in 3.7 mL toluene was added diphosphorus pentasulfide(156 mg, 1.1 eq.). The mixture was heated for 4 hours at 110° C. Waterwas added and the aqueous phase was extracted with ethyl acetate. Theseparated organic layer was washed with saturated sodium chloridesolution and dried with magnesium sulfate. Then the solvent was removedunder reduced pressure and the crude product was purified by columnchromatography (cyclohexane, ethyl acetate) to afford the desiredproduct as a colorless solid (152 mg, 69%). LC/MS: Retention time(R_(t)) 1.298 min, ¹H NMR (500 MHz, CDCl₃): δ [ppm]=8.05-8.18 (2H), 7.27& 7.43 (2H), 5.45 & 4.95 (2H), 3.48 & 3.25 (3H), 2.89 (2H), 1.38 (3H).

I.6) Preparation of N′-hydroxy-4-(methylaminomethyl)benzamidine

To a solution of 4-(methylaminomethyl)benzonitrile (61.4 g, 1 eq.) andtrimethylamine (106 g, 2.5 eq.) in ethanol (500 mL) hydroxylaminehydrochloride (58.4 g, 2 eq.) was added. The mixture was heatedovernight at 80° C. After cooling to room temperature, the solvent wasremoved under reduced pressure. The title compound was used directlywithout further purification.

I.7) Preparation ofN-methyl-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanamine

A solution of N′-hydroxy-4-(methylaminomethyl)benzamidine (25.5 g, 1eq.) in dichloromethane (200 mL) was treated with trifluoroaceticanhydride (119 g, 4 eq.). The resulting mixture was stirred overnight atambient temperature, before it was diluted with water and washed withdichloromethane. The combined organic layer was washed with an aqueoussolution of sodium hydrogencarbonate, dried with magnesium sulfate andfreed from solvent. The residue (dark oil) was used directly withoutfurther purification (42.4 g).

I.8) Preparation ofN-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]ethanesulfonamide(Ex-18, Example not According to the Invention)

To a solution ofN-methyl-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanamine(400 mg, 1.0 eq.) in dichloromethane (2 mL) was added trimethylamine(377 mg, 2.4 eq.) and ethanesulfonyl chloride (240 mg, 1.2 eq.)dropwise. The mixture was stirred at room temperature until HPLCindicated complete conversion of the starting material. After washingwith an aqueous solution of hydrochloric acid (1N) the organic layer wasdried with magnesium sulfate and the solvent was removed under reducedpressure. The crude product was purified by column chromatography(cyclohexane:ethyl acetate) to afford the desired product as a colorlesssolid (130 mg, 24%). Melting point: 53° C., LC/MS: Retention time 1.163min., ¹H NMR (400 MHz, CDCl₃): δ [ppm]=8.1 (2H), 7.5 (2H), 4.4 (2H), 3.1(2H), 2.8 (3H), 1.4 (3H).

I.9) Preparation of 4-[1-(methylamino)ethyl]benzonitrile

To a solution of 4-(1-bromoethyl)benzonitrile (3.2 g, 1 eq.) intetrahydrofurane (50 mL) methylamine (11.8 g of a 40% solution byweight, 10 eq.) was added. The mixture was stirred overnight at roomtemperature. After removing the solvent under reduced pressure, anaqueous solution of sodium chloride was added and the aqueous mixturewas extracted with ethyl acetate. The combined organic layer was driedover magnesium sulfate and freed from solvent. The title compound (2.2g) was used directly without further purification.

I.10) Preparation of N′-hydroxy-4-[1-(methylamino)ethyl]benzamidine

A solution of 4-[1-(methylamino)ethyl]benzonitrile (2.2 g, 1 eq.),hydroxylamine hydrochloride (1.5 g, 2 eq.), triethylamine (2.8 g, 2.5eq.) and ethanol (40 mL) was stirred overnight at room temperature. Theorganic solvent was removed under reduced pressure. The title compound(2.1 g) was used directly without further purification.

I.11) Preparation ofN-methyl-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanamine

A solution of N′-hydroxy-4-[1-(methylamino)ethyl]benzamidine (2.1 g, 1eq.) in dichloromethane (30 mL) was treated with trifluoroaceticanhydride (8.1 g, 5 eq.). The resulting mixture was stirred overnight atambient temperature, before it was diluted with water and washed withdichloromethane. The combined organic layer was washed with an aqueoussolution of sodium hydrogencarbonate, dried with magnesium sulfate andfreed from solvent. The residue (2.46 g) was used directly withoutfurther purification.

I.12) Preparation ofN-methyl-N-[1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]propanamide

To a solution ofN-methyl-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanamine(0.35 g, 1 eq.) in dichloromethane (5 mL) and triethylamine (0.2 g, 2.2eq.) gradually propionyl chloride (0.91 g, 1.1 eq.) was added. Themixture was stirred at room temperature until HPLC indicated completeconversion of the starting material. The solvent was removed underreduced pressure, water was added and the aqueous layer was extractedwith ethyl acetate. The organic layer was poured into dichloromethaneand washed with an aqueous solution of hydrochloric acid (1N solution)followed by an aqueous solution of sodium hydrogen carbonate. Theorganic layer was dried over magnesium sulfate and the solvent wasremoved under reduced pressure. The crude product was purified by columnchromatography to afford the desired product as a colorless oil (0.23 g,78%). LC/MS: Retention time (R_(t)) 1.19 min, ¹H NMR (400 MHz, CDCl₃): δ[ppm]=8.1 (2H), 7.4 (2H), 6.14 (1H), 2.7 (3H), 2.4 (2H), 1.6 (1H), 1.5(2H) 1.2 (3H).

I.13) Preparation ofN-methyl-N-[1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]propanethioamide(Ex-8)

To a solution ofN-methyl-N-[1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]-propanamide(0.20 g, 1 eq.) in 3.6 mL toluene was added diphosphorus pentasulfide(149 mg, 1.1 eq.). The mixture was heated for 4 hours at 110° C. Waterwas added and the aqueous phase was extracted with ethyl acetate. Theseparated organic layer was washed with saturated sodium chloridesolution and dried with magnesium sulfate. The solvent was removed underreduced pressure and the crude product was purified by columnchromatography (cyclohexane, ethyl acetate) to afford the desiredproduct as a colorless solid (167 mg, 95%). LC/MS: Retention time(R_(t)) 1.35 min, ¹H NMR (500 MHz, CDCl₃): δ [ppm]=8.18 (d, 2H), 7.49(d, 2H), 7.46 (q, 1H), 2.80-3.21 (5H), 1.31-1.78 (6H).

I.14) Preparation of N-[1-(4-cyanophenyl)ethyl]methanesulfonamide

To a solution of 4-(1-aminoethyl)benzonitrile (400 mg, 1.0 eq.) inethanol (5 mL) was added trimethylamine (553 mg, 2 eq.) andmethanesulfonyl chloride (313 mg, 1 eq.) dropwise. The mixture wasstirred at room temperature until HPLC indicated complete conversion ofthe starting material. After washing with an aqueous solution ofhydrochloric acid (1N) the organic layer was dried with magnesiumsulfate and the solvent was removed under reduced pressure. The titlecompound (0.61 g) was used directly without further purification.

I.15) Preparation ofN′-hydroxy-4-[1-(methanesulfonamido)ethyl]benzamidine

A solution of N-[1-(4-cyanophenyl)ethyl]methanesulfonamide (0.40 g, 1eq.), hydroxylamine hydrochloride (0.25 g, 2 eq.), triethylamine (0.36g, 2 eq.) and ethanol (5 mL) was stirred overnight at room temperature.The organic solvent was removed under reduced pressure. The titlecompound (0.46 g) was used directly without further purification.

I.16) Preparation ofN-[1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]methanesulfonamide(Ex-30)

A solution of N′-hydroxy-4-[1-(methanesulfonamido)ethyl]benzamidine (450mg, 1.0 eq.) in methylene chloride (10 mL) was treated withtrifluoroacetic anhydride (1.1 g, eq.). The resulting mixture wasstirred overnight at ambient temperature, before it was diluted withwater and washed with dichloromethane. The combined organic layer waswashed with an aqueous solution of sodium hydrogencarbonate, dried withmagnesium sulfate and freed from solvent. The and the crude product waspurified by column chromatography (0.10 g, 16%) to afford the desiredproduct. L/MS: Retention time 1.09 min., ¹H NMR (400 MHz, CDCl₃): δ[ppm]=8.15 (d, 2H), 7.51 (d, 2H), 4.75 (q, 1H),4.64 (s, 1H), 2.75 (s,3H), 1.56 (d, 3H).

Compounds Ex-1 to Ex-47 in Table I were prepared in analogy to theprocedures described above.

TABLE I Compounds Ex-1 to Ex-47 of formula I.Ex, wherein the meaning ofR¹, R², R³, R⁴ and L is as defined in each line.

Melting HPLC R_(t) point Ex. no R¹ R² R³/R⁴ L (min)** (° C.) Ex-1 CH₃CH₃ H/CH₃ —C(═S)— 1.28 62 Ex-2 iso-propyl CH₃ H/CH₃ —C(═S)— 1.42 77 Ex-3* ethyl iso-propyl H/H —C(═S)— 1.38 — Ex-4 propyl CH₃ H/CH₃ —C(═S)—1.41 —  Ex-5* propyl CH₃ H/H —C(═S)— 1.36 —  Ex-6* 2-butyl CH₃ H/H—C(═S)— 1.42 —  Ex-7* ethyl CH₃ H/H —C(═S)— 1.30 63 Ex-8 ethyl CH₃ H/CH₃—C(═S)— 1.35 —  Ex-9* tert-butyl iso-propyl H/H —C(═S)— 1.49 — Ex-10*iso-propyl CH₃ H/H —C(═S)— 1.33 73 Ex-11* 3-pentyl CH₃ H/H —C(═S)— 1.4771 Ex-12* CH₃ allyl H/H —C(═S)— 1.32 — Ex-13* CH₃ CH₃ H/H —C(═S)— 1.2286 Ex-14* CH₃ iso-propyl H/H —SO₂— 1.22 — Ex-15* propyl iso-propyl H/H—SO₂— 1.34 — Ex-16* ethyl iso-propyl H/H —SO₂— 1.29 — Ex-17* CH₃ CH₃ H/H—SO₂— 1.11 — Ex-18* ethyl CH₃ H/H —SO₂— 1.16 53 Ex-19* propyl CH₃ H/H—SO₂— 1.25 91 Ex-20* propyl ethyl H/H —SO₂— 1.27 83-88 Ex-21* CH₃ ethylH/H —SO₂— 1.17 64-67 Ex-22* iso-propyl CH₃ H/H —SO₂— 1.22 124-129 Ex-23*ethyl ethyl H/H —SO₂— 1.22 96 Ex-24* iso-propyl iso-propyl H/H —SO₂—0.98 137 Ex-25* CH₃ 3-pentyl H/H —SO₂— 1.32 — Ex-26* CH₃ cyclopropyl H/H—SO₂— 1.18 88-89 Ex-27* ethyl cyclopropyl H/H —SO₂— 1.22 87 Ex-28*propyl cyclopropyl H/H —SO₂— 1.28 89 Ex-29* 2-butyl CH₃ H/H —SO₂— 1.3088 Ex-30  CH₃ H H/CH₃ —SO₂— 1.09 — Ex-31  ethyl H H/CH₃ —SO₂— 1.13 —Ex-32  3-pentyl H H/CH₃ —SO₂— 1.29 — Ex-33* 2,2,2- CH₃ H/H —SO₂— 1.27113-115 trifluoroethyl Ex-34* 2,2- CH₃ H/H —SO₂— 1.26 93 difluoropropylEx-35* 2,2,2- CH₃ H/H —SO₂— 1.29 110 trifluoro-1- methyl-ethyl Ex-36*2,2- CH₃ H/H —SO₂— 1.23 92 difluoroethyl Ex-37* 2,2,2- ethyl H/H —SO₂—1.30 97 trifluoroethyl Ex-38* 2,2,2- ethyl H/H —SO₂— 1.32 110trifluoro-1- methyl-ethyl Ex-39* 2,2- ethyl H/H —SO₂— 1.26 76difluoroethyl Ex-40* 2,2- ethyl H/H —SO₂— 1.30 88 difluoropropyl Ex-41*2,2,2- cyclopropyl H/H —SO₂— 1.32 108 trifluoroethyl Ex-42* 2,2,2-cyclopropyl H/H —SO₂— 1.34 83 trifluoro-1- methyl-ethyl Ex-43* 2,2-cyclopropyl H/H —SO₂— 1.25 62 difluoroethyl Ex-44* 2,2- cyclopropyl H/H—SO₂— 1.28 90 difluoropropyl Ex-45* 2,2,2- CH₃ H/CH₃ —SO₂— 1.27 124trifluoroethyl Ex-46* 2,2- CH₃ H/CH₃ —SO₂— 1.26 96 difluoroethyl Ex-47*2,2,2- allyl H/H —SO₂— 1.33 73 trifluoroethyl *compound not according tothe invention **HPLC: High Performance Liquid Chromatography;HPLC-column Kinetex XB C18 1.7μ (50 × 2.1 mm); eluent:acetonitrile/water + 0.1% trifluoroacetic acid (gradient from 5:95 to100:0 in 1.5 min at 60° C., flow gradient from 0.8 to 1.0 ml/min in 1.5min). MS: Quadrupol Electrospray Ionisation, 80 V (positive mode).R_(t): retention time in minutes.

II. BIOLOGICAL EXAMPLES FOR FUNGICIDAL ACTIVITY

The fungicidal action of the compounds of formula I was demonstrated bythe following experiments: The spray solutions were prepared in severalsteps: The stock solution were prepared by mixing acetone and/ordimethylsulfoxide and the wetting agent/emulsifier Wettol, which isbased on ethoxylated alkylphenoles, in a relation (volume)solvent-emulsifier of 99 to 1. This mixture was added to 25 mg of thecompound to give a total of 5 mL. Water was then added to total volumeof 100 mL. This stock solution was diluted with the describedsolvent-emulsifier-water mixture to the given concentration.

II.1) Curative Control of Soy Bean Rust on Soy Beans Caused byPhakopsora pachyrhizi

Leaves of pot-grown soy bean seedlings were inoculated with spores ofPhakopsora pachyrhizi. To ensure the success of the artificialinoculation, the plants were transferred to a humid chamber with arelative humidity of about 95% and 20 to 24° C. for 24 hours. The nextday the plants were cultivated for 3 days in a greenhouse chamber at 23to 27° C. and a relative humidity between 60 and 80%. Then the plantswere sprayed to run-off with an aqueous suspension, containing theconcentration of active ingredient or their mixture as described below.The plants were allowed to air-dry. Then the trial plants werecultivated for 14 days in a greenhouse chamber at 23 to 27° C. and arelative humidity between 60 and 80%. The extent of fungal attack on theleaves was visually assessed as % diseased leaf area.

In this test, the plants which had been treated with 32 ppm of theactive compounds Ex-1, Ex-2, Ex-3, Ex-4, Ex-5, Ex-6, Ex-7, Ex-10, Ex-11,Ex-12 and Ex-13 showed a diseased leaf area of at most 20%, whereas theuntreated plants showed 90% diseased leaf area.

In this test, the plants which had been treated with 32 ppm of theactive compounds Ex-14, Ex-16, Ex-17, Ex-18 and Ex-19 showed a diseasedleaf area of at most 2%, whereas the untreated plants showed 100%diseased leaf area.

In this test, the plants which had been treated with 63 ppm of theactive compounds Ex-20, Ex-21, Ex-22, Ex-23, Ex-26, Ex-27, Ex-29, Ex-30,Ex-31, Ex-32, Ex-35, Ex-36, Ex-37, Ex-39, Ex-40, Ex-41, Ex-43, Ex-44 andEx-46 showed a diseased leaf area of at most 16%, whereas the untreatedplants showed 90% diseased leaf area.

II.2) Protective Control of Soy Bean Rust on Soy Beans Caused byPhakopsora pachyrhizi

Leaves of pot-grown soy bean seedlings were sprayed to run-off with anaqueous suspension, containing the concentration of active ingredient ortheir mixture as described below. The plants were allowed to air-dry.The trial plants were cultivated for 2 day in a greenhouse chamber at 23to 27° C. and a relative humidity between 60 and 80%. Then the plantswere inoculated with spores of Phakopsora pachyrhizi. To ensure thesuccess the artificial inoculation, the plants were transferred to ahumid chamber with a relative humidity of about 95% and 20 to 24° C. for24 hours. The trial plants were cultivated for fourteen days in agreenhouse chamber at 23 to 27° C. and a relative humidity between 60and 80%. The extent of fungal attack on the leaves was visually assessedas % diseased leaf area.

In this test, the plants which had been treated with 32 ppm of theactive compounds Ex-1, Ex-2, Ex-3, Ex-4, Ex-5, Ex-6, Ex-7, Ex-8, Ex-9,Ex-10, Ex-11, Ex-12, Ex-13 Ex-14, Ex-15, Ex-16, Ex-17, Ex-18 and Ex-19showed a diseased leaf area of at most 5%, whereas the untreated plantsshowed 100% diseased leaf area.

In this test, the plants which had been treated with 63 ppm of theactive compounds Ex-20, Ex-21, Ex-22, Ex-23, Ex-25, Ex-26, Ex-27, Ex-28,Ex-29, Ex-30, Ex-31, Ex-32, Ex-35, Ex-36, Ex-37, Ex-38, Ex-39, Ex-40,Ex-41, Ex-42, Ex-43, Ex-44, Ex-45 and Ex-46 showed a diseased leaf areaof at most 7%, whereas the untreated plants showed 90% diseased leafarea.

II.3) Curative Control of Brown Rust on Wheat Caused by Pucciniarecondita

The first two developed leaves of pot-grown wheat seedling were dustedwith spores of Puccinia recondita. To ensure the success the artificialinoculation, the plants were transferred to a humid chamber withoutlight and a relative humidity of 95 to 99% and 20 to 24° C. for 24hours. The next day the plants were cultivated for 3 days in agreenhouse chamber at 20 to 24° C. and a relative humidity between 65and 70%. Then the plants were sprayed to run-off with an aqueoussuspension, containing the concentration of active ingredient or theirmixture as described below. The plants were allowed to air-dry. Then thetrial plants were cultivated for 8 days in a greenhouse chamber at 20 to24° C. and a relative humidity between 65 and 70%. The extent of fungalattack on the leaves was visually assessed as % diseased leaf area.

In this test, the plants which had been treated with 63 ppm of theactive compounds Ex-1, Ex-2, Ex-3, Ex-5, Ex-6, Ex-7, Ex-8, Ex-10, Ex-11,Ex-13, Ex-14, Ex-17 and Ex-18 showed a diseased leaf area of at most15%, whereas the untreated plants showed 90% diseased leaf area.

In this test, the plants which had been treated with 63 ppm of theactive compounds Ex-21, Ex-22, Ex-23, Ex-26, Ex-27, Ex-29, Ex-30, Ex-31,Ex-36 and Ex-39 showed a diseased leaf area of at most 9%, whereas theuntreated plants showed 90% diseased leaf area.

II.4) Preventative Control of Brown Rust on Wheat Caused by Pucciniarecondita

The first two developed leaves of pot-grown wheat seedling were sprayedto run-off with an aqueous suspension, containing the concentration ofactive ingredient or their mixture as described below. The next day theplants were inoculated with spores of Puccinia recondita. To ensure thesuccess the artificial inoculation, the plants were transferred to ahumid chamber without light and a relative humidity of 95 to 99% and 20to 24° C. for 24 hours. Then the trial plants were cultivated for 6 daysin a greenhouse chamber at 20-24° C. and a relative humidity between 65and 70%. The extent of fungal attack on the leaves was visually assessedas % diseased leaf area.

In this test, the plants which had been treated with 63 ppm of theactive compounds Ex-14, Ex-16, Ex-17, Ex-18 and Ex-19 showed a diseasedleaf area of at most 5%, whereas the untreated plants showed 80%diseased leaf area.

In this test, the plants which had been treated with 63 ppm of theactive compounds Ex-20, Ex-21, Ex-22, Ex-23, Ex-25, Ex-26, Ex-27, Ex-28,Ex-29, Ex-30, Ex-31, Ex-36, Ex-37, Ex-39, Ex-40 and Ex-43 showed adiseased leaf area of at most 15%, whereas the untreated plants showed90% diseased leaf area.

The invention claimed is:
 1. A compound of the formula I, or an N-oxide,or an agriculturally acceptable salt thereof;

wherein: R^(A) is independently selected from the group consisting ofhalogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy andC₁-C₆-haloalkoxy; n is 0, 1 or 2; L is —(C═S)—; R¹ is C₁-C₆-alkyl orC₁-C₆-alkoxy; wherein any of the aliphatic groups are unsubstituted orsubstituted with 1, 2, 3, 4, 5 or up to the maximum possible number ofidentical or different radicals selected from the group consisting ofhydroxy, cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy and C₃-C₈-cycloalkyl; R² ishydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkenyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl,phenyl-C₁-C₄-alkyl, phenyl, C(═O)—(C₁-C₆-alkyl) or C(═O)—(C₁-C₆-alkoxy);and wherein any of the aliphatic or cyclic groups are unsubstituted orsubstituted with 1, 2, 3 or up to the maximum possible number ofidentical or different radicals selected from the group consisting ofhalogen, hydroxy, cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy and C₃-C₈-cycloalkyl;R³, R⁴ independently of each other are selected from the groupconsisting of hydrogen, halogen, cyano, C₁-C₄-alkyl, C₁-C₄-alkenyl,C₁-C₄-alkynyl, C₁-C₄-haloalkyl and C₁-C₄-alkoxy; or R³ and R⁴ togetherwith the carbon atom to which they are bound form a saturated 3- to7-membered carbocycle or a saturated 3- to 6-membered heterocycle;wherein the saturated heterocycle includes beside carbon atoms 1, 2 or 3heteroatoms independently selected from the group consisting of N, O andS as ring member atoms; and wherein said N ring member atom issubstituted with the group R^(N); wherein R^(N) is hydrogen, C₁-C₆-alkylor halogen; and wherein said S ring member atom is unsubstituted orsubstituted with 1 or 2 oxo radicals; and wherein one or two CH₂ groupsof the saturated carbocycle or of the saturated heterocycle may bereplaced by one or two groups independently selected from —C(═O)— and—C(═S)—; and wherein the carbon ring member atoms of the saturatedcarbocycle or of the saturated heterocycle are unsubstituted orsubstituted with a total number of 1, 2, 3, 4 or up to the maximumpossible number of identical or different radicals selected from thegroup consisting of halogen, cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy andC₃-C₈-cycloalkyl; with the exception of compounds of the formula Iwherein R³ and R⁴ both are hydrogen.
 2. The compound of claim 1 havingformula I.1, or an N-oxide, or an agriculturally acceptable salt thereof

wherein n is 0 or
 1. 3. The compound of claim 1, wherein n is
 0. 4. Thecompound of claim 1, wherein R³ and R⁴ are independently selected fromthe group consisting of hydrogen, halogen, C₁-C₆-alkyl andC₁-C₆-haloalkyl; or R³ and R⁴ together with the carbon atom to whichthey are bound form a cyclopropyl ring; with the exception of compoundsof the formula I wherein R³ and R⁴ both are hydrogen.
 5. The compound ofclaim 1, wherein R³ is hydrogen and R⁴ is methyl or trifluoromethyl. 6.The compound of claim 1, wherein R³ and R⁴ together with the carbon atomto which they are bound form a cyclopropyl ring.
 7. The compound ofclaim 1, wherein R¹ is C₁-C₆-alkyl; unsubstituted or substituted with 1,2, 3 or up to the maximum possible number of identical or differentradicals selected from the group consisting of C₁-C₆-alkoxy andC₃-C₈-cycloalkyl.
 8. The compound of claim 1, wherein R² is hydrogen,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkyl-C₁-C₄-alkyl or phenyl; and wherein any of the aliphaticor cyclic groups are unsubstituted or substituted with 1, 2, 3, 4 or upto the maximum possible number of identical or different radicalsselected from the group consisting of halogen, cyano, C₁-C₆-alkyl andC₁-C₆-alkoxy.
 9. The compound of claim 1, wherein R² is hydrogen,C₁-C₆-alkyl, C₁-C₆-alkenyl, ethynyl, propargyl, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkyl-C₁-C₄-alkyl or phenyl; and wherein any of the aliphaticor cyclic groups are unsubstituted or substituted with 1, 2, 3, 4 or upto the maximum possible number of identical or different radicalsselected from the group consisting of halogen and C₁-C₆-alkyl; and R¹ isC₁-C₆-alkyl.
 10. An agrochemical composition, which comprises anauxiliary and at least one compound of the formula I, or an N-oxide, oran agriculturally acceptable salt thereof, as defined in claim
 1. 11.The agrochemical composition of claim 10, wherein the auxiliary isselected from the group of ionic or non-ionic surfactants.
 12. Seedtreated with the composition of claim 10, wherein the amount of thecompound of the formula I, or an N-oxide, or an agriculturallyacceptable salt thereof, is from 0.1 g to 10 kg per 100 kg of seed. 13.A method for combating phytopathogenic harmful fungi, which processcomprises treating the fungi, the plants, the soil or seeds to beprotected against fungal attack, with an effective amount of at leastone compound of formula I, or an N-oxide, or an agriculturallyacceptable salt thereof, as defined in claim
 1. 14. The method of claim13, wherein the compound of formula I is a compound of formula I.1, oran N-oxide, or an agriculturally acceptable salt thereof

wherein n is 0 or
 1. 15. The method of claim 13, wherein R³ and R⁴ areindependently selected from the group consisting of hydrogen, halogen,C₁-C₆-alkyl and C₁-C₆-haloalkyl; or R³ and R⁴ together with the carbonatom to which they are bound form a cyclopropyl ring; with the exceptionof compounds of the formula I wherein R³ and R⁴ both are hydrogen. 16.The method of claim 13, wherein R³ is hydrogen and R⁴ is methyl ortrifluoromethyl.
 17. The method of claim 13, wherein R³ and R⁴ togetherwith the carbon atom to which they are bound form a cyclopropyl ring.18. The method of claim 13, wherein R¹ is C₁-C₆-alkyl; unsubstituted orsubstituted with 1, 2, 3 or up to the maximum possible number ofidentical or different radicals selected from the group consisting ofC₁-C₆-alkoxy and C₃-C₈-cycloalkyl.
 19. The method of claim 13, whereinR² is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkyl-C₁-C₄-alkyl or phenyl; and wherein any of the aliphaticor cyclic groups are unsubstituted or substituted with 1, 2, 3, 4 or upto the maximum possible number of identical or different radicalsselected from the group consisting of halogen, cyano, C₁-C₆-alkyl andC₁-C₆-alkoxy.
 20. The method of claim 13, wherein R² is hydrogen,C₁-C₆-alkyl, C₁-C₆-alkenyl, ethynyl, propargyl, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkyl-C₁-C₄-alkyl or phenyl; and wherein any of the aliphaticor cyclic groups are unsubstituted or substituted with 1, 2, 3, 4 or upto the maximum possible number of identical or different radicalsselected from the group consisting of halogen and C₁-C₆-alkyl; and R¹ isC₁-C₆-alkyl.